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Hamzeh Kiyani

Associate Professor of Organic Chemistry

Biography

Dr. Hamzeh Kiyani has received his Ph.D. in Organic Chemistry from Guilan University under the supervision of Professor Nosratollah Mahmoodi, Iran in 2009. He also holds M.Sc. degree in Organic Chemistry from the same University. He started his career as an Assistant Professor at the Damghan University in 2010. His research interests focus on the development of new methodology for organic synthesis, green chemistry, organic photochromism, and synthesis of heterocyclic compounds. He has published more than 60 scientific papers. He has been selected as a distinguished researcher in the School of Chemistry at the Damghan University within 2014-2016. Currently he is an Associate Professor at the Damghan University.

Teaching

  • Advanced Stereochemistry (Ph.D.)
  • Advanced Organic Synthesis (Ph.D.)
  • Advanced Organic Chemistry (M.Sc.)
  • Physical Organic Chemistry (M.Sc. and B.Sc.)
  • New Topics in Organic Chemistry (M.Sc.)
  • Medicinal Chemistry (B.Sc.)
  • Organic Synthesis (B.Sc.)
  • Organic Chemistry I, II, III (B.Sc.)
  • Organic Chemistry Laboratory I, II (B.Sc.)
  • Separation and Identification of Organic Compounds (B.Sc.)
  • General Chemistry I, II (B.Sc.)
  • General Chemistry Laboratory, I, II (B.Sc.)
  • Biochemistry (B.Sc.)
  • Environmental Chemistry (B.Sc.)
  • The Application of Spectroscopy in Organic Chemistry (B.Sc.)

Selected Publications

Kiyani, H., Bamdad, M. Sodium ascorbate as an expedient catalyst for green synthesis of polysubstituted 5-aminopyrazole-4-carbonitriles and 6-amino-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles (2018) Research on Chemical Intermediates, 44 (4), pp. 2761-2778.

DOI: 10.1007/s11164-018-3260-0

Sodium ascorbate (SA) was used as a safe catalyst for the synthesis of 5-aminopyrazole-4-carbonitriles from the one-pot three-component cyclocondensation (3-CC) of aldehydes, phenylhydrazine, and malononitrile at 50 °C. This 3-CC proceeds in a mixture of ethanol–water as a green reaction medium to give the desired densely functionalized pyrazoles in good to high yields. 6-Amino-1,4-dihydropyrano-[2,3-c]pyrazole-5-carbonitriles were also synthesized in the presence of SA via an eco-friendly and simple four-component cyclocondensation (4-CC). This 4-CC performed in refluxing water as a green medium and dihydropyrano-[2,3-c]pyrazole products were obtained in excellent yields and relatively shorter reaction times. These environmentally friendly multicomponent cyclocondensations offer some interesting advantages, including time-saving, easily available starting materials, mild conditions, minimizing the amount of waste, good atom efficiency, avoiding hazardous organic solvents or catalysts, and the ease of the work-up. © 2018, Springer Science+Business Media B.V., part of Springer Nature.

AUTHOR KEYWORDS: 5-Aminopyrazole-4-carbonitrile; 6-Amino-1,4-dihydropyrano-[2,3-c]pyrazole-5-carbonitrile; Green; Hydrazine; Phenylhydrazine; Sodium ascorbate
INDEX KEYWORDS: Catalysts; Hydrazine; Nitrogen compounds, 5-Aminopyrazole-4-carbonitrile; Green; Phenylhydrazine; Pyrazoles; Sodium ascorbate, Sodium
PUBLISHER: Springer Netherlands

Sudhan, S.P.N., Ahmed, R.N., Kiyani, H., Mansoor, S.S. Ionic liquid 1-butyl-3-methylimidazolium bromide: A green reaction media for the efficient synthesis of 3-methyl-1,4-diphenyl-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidine-6-ones/thiones using phthalimide-N-sulfonic acid as catalyst (2018) Journal of Saudi Chemical Society, 22 (3), pp. 269-278.

DOI: 10.1016/j.jscs.2016.07.001

A simple, green and environmentally benign procedure was developed for the one pot synthesis of 3-methyl-1,4-diphenyl-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidine-6-one/thiones using catalytic amount of phthalimide-N-sulfonic acid (PISA) in 1-butyl-3-methylimidazolium bromide ([Bmim][Br]) ionic liquid via the three-component reaction of 1-phenyl-3-methyl-1H-pyrazole-5(4H)-one, aromatic aldehyde and urea/thiourea. [Bmim][Br] as reaction media offers several advantages including non-toxic, non-corrosive, shorter reaction times, high yield of the products, mild reaction conditions as well as simple experimental and isolation procedures. © 2016 King Saud University

AUTHOR KEYWORDS: 1-Butyl-3-methylimidazolium bromide ([Bmim][Br]); 1-Phenyl-3-methyl-1H-pyrazole-5(4H)-one; Phthalimide-N-sulfonic acid (PISA); Pyrazolo[3,4-d]pyrimidine
PUBLISHER: Elsevier B.V.

Kiyani, H. Recent advances in three-component cyclocondensation of dimedone with aldehydes and malononitrile for construction of tetrahydrobenzo[b]pyrans using organocatalysts (2018) Current Organic Synthesis, 15 (8), pp. 1043-1072.

DOI: 10.2174/1570179415666181031124459


Background: The majority of naturally occurring compounds, pharmaceuticals, and drug-candidate molecules possess heterocyclic scaffolds. In this context, tetrahydobenzo[b]pyrans are of considerable importance. In the line with the synthesis of these valuable heterocyclic compounds, the researchers tried to synthesize these molecules using different organocatalysts. The development of new strategies for three-component condensation of dimedone, various aldehydes and malononitrile for construction of tetrahydrobenzo[b]pyrans is of particular interest to organic chemists and pharmacologists. Objective: In this review, three-component catalyzed synthesis of tetrahydrobenzo[b]pyran compounds is introduced, focusing on the developments in the use of organocatalysts. Organocatalytic approaches were investigated for the synthesis of tetrahydrobenzo[b]pyrans. This contribution covers the literature concerning the synthesis of heterocycles referred to, in recent times. Conclusion: This review article is associated with the study of the three-component synthesis of tetrahydrobenzo[b]pyrans using organocatalysts. This review also provides an insight into the importance of these heterocycles. In the vast majority of these reactions, water and water-ethanol system have been used as green solvent media for implementation of them. The use of green solvents, the development of less toxic and promising reagents/catalysts as well as the design of inexpensive and reliable approaches are some of the principles of green chemistry, and most of the methods are benefited from them. Tetrahydrobenzo[b]pyrans and organocatalysts open avenue ofnew horizons. The recyclability of the many of these organocatalysts offers an additional merit for the use of these catalysts in 3-CR of aldehydes, dimedone, and malononitrile reactions. © 2018 Bentham Science Publishers.

AUTHOR KEYWORDS: Arylaldehyde; Dimedone; Green solvent; Malononitrile; Organocatalyst; Tetrahydrobenzo[b]pyrans; Three-component reaction
PUBLISHER: Bentham Science Publishers B.V.

Kiyani, H., Mosallanezhad, A. Sulfanilic acid-catalyzed synthesis of 4-arylidene-3-substituted isoxazole-5(4H)-ones (2018) Current Organic Synthesis, 15 (5), pp. 715-722.

DOI: 10.2174/1570179415666180423150259

Aim and Objective: In recent studies, chemistry of heterocyclic compounds, especially isoxazoles, has been widely considered by organic chemistry researchers because they have been found in many molecules, including naturally occurring bioactive compounds, pharmaceuticals, and agrichemicals. Isoxazol- 5(4H)-ones and their derivatives, on the other hand, have significant biological properties can be mentioned as examples of antibacterial, anti-inflammatory, antifungal, anticancer, analgesic, fungicidal, and insecticidal activities. Therefore, the development of ecofriendly methods, such as three-component processes, for the synthesis of isoxazol-5(4H)-ones is highly desirable. This work focus on the one-pot, three-component reaction (3-CR) of aldehydes, hydroxylamine hydrochloride, and three β-ketoester using catalytic amounts of sulfanilic acid (SA) aimed at the synthesis of isoxazol-5(4H)-ones. Another aim of this study is to use water as a green solvent for the above-mentioned 3-CR. Materials and Methods: Using SA as an efficient organocatalyst, the multicomponent cyclocondensation of aromatic/hetero-aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/ethyl 4- chloroacetoacetate/ethyl benzoylacetate has been implemented. The reactions were carried out in water as a green solvent at room temperature. The corresponding heterocyclic products were separated by simple filtration and washing with water. Also, the solvent was removed from the filtrate by evaporation to recycle the catalyst. Results: It was found that SA act as the catalyst for the synthesis of 4-arylidene-3-substituted isoxazole-5(4H)- ones via three-component reaction of aromatic/hetero-aromatic aldehydes, hydroxylamine hydrochloride, and three β-dicarbonyl compounds (ethyl acetoacetate, ethyl 4-chloroacetoacetate, and ethyl benzoylacetate). Optimization of the catalyst quantity and solvent showed that the highest yield was achieved with 20 mol% of SA in aqueous media. 4-Arylidene-3-substituted isoxazole-5(4H)-ones have been successfully synthesized in the presence of SA catalyst. Conclusion: The SA catalyst could be recovered easily from the filtrate via evaporation of solvent and reused many times. The present synthetic method is a simple, green, clean, and environmentally friendliness alternative for synthesizing 4-arylidene-3-substituted isoxazole-5(4H)-ones. Reactions were performed without the use of heating, microwave and ultrasound irradiations. © 2018 Bentham Science Publishers.

AUTHOR KEYWORDS: 4-Arylidene-3-substituted isoxazole-5(4H)-ones; Green; Sulfanilic acid; Three-component; Water; β-dicarbonyl
PUBLISHER: Bentham Science Publishers B.V.

Kiyani, H., Aslanpour, S. Sulfanilic acid-catalyzed green synthesis of 4-Arylidene-2-phenyl-5(4H)-Oxazolones (2018) Heterocycles, 96 (2), pp. 297-303.

DOI: 10.3987/COM-17-13847

This study is focused on the catalytic activity of sulfanilic acid (SA) in the straightforward synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones via condensation of aromatic aldehydes, hippuric acid, and acetic anhydride under green experimental conditions (water solvent). The catalyst could be recovered easily from the filtrate via evaporation of the solvent and reused many times. It was found that the method is clean, relatively rapid, and environmentally friendliness alternative for the synthesis of Erlenmeyer-Plöchl azlactones as well as no needed for heating, microwave and ultrasound irradiations. Furthermore, all of the substrates and catalyst are easily accessible and inexpensive. © 2018 The Japan Institute of Heterocyclic Chemistry.

PUBLISHER: Japan Institute of Heterocyclic Chemistry

Mosallanezhad, A., Kiyani, H. KI-mediated three-component reaction of hydroxylamine hydrochloride with aryl/heteroaryl aldehydes and two β-oxoesters (2018) Orbital, 10 (2), pp. 133-139.

DOI: 10.17807/orbital.v10i2.1134

A KI-mediated multi-component cyclocondensation of hydroxylamine hydrochloride, aromatic/hetero-aromatic aldehydes, and ethyl acetoacetate or 4-chloroethyl acetoacetate to form isoxazole-5(4H)-one heterocycles is described. The reaction employs readily accessible starting reactants and provides a range of synthetically isoxazole-5(4H)-ones in good to high yields. Reactions were performed in water as a green medium at room temperature (rt) without heating, microwave irradiation or sonication. Reusability of the reaction medium is also a noteworthy characteristic of this reaction. © 2018, Universidade Federal de Mato Grosso do Sul, Departamento de Quimica. All rights reserved.

AUTHOR KEYWORDS: Green; Isoxazole-5(4H)-ones; Potassium iodide; Water; β-dicarbonyl
PUBLISHER: Universidade Federal de Mato Grosso do Sul, Departamento de Quimica

Banari, H., Kiyani, H., Pourali, A. Green synthesis of bis(indolyl)methanes catalysed by salicylic acid (2018) Chiang Mai Journal of Science, 45 (1), pp. 413-420.

In this contribution, salicylic acid (SA) has been used to catalyze synthesis of a series of biologically relevant 3,3′-bis(indolyl)methanes (BIMs) via the electrophilic substitution of indole derivatives on aldehyde compounds. The optimum catalyst loading was observed at 15 mol%. The procedure is simple and the expected bis-heterocyclic compounds were isolated in good to high yields. The present protocol provides the advantages of convenience, mild reaction conditions, eco-friendliness, energy-saving, and no use of hazardous solvents. © 2018, Chiang Mai University. All rights reserved.

AUTHOR KEYWORDS: 2-methylindole; 3,3′-bis(indolyl)methanes; Green; Indole; Salicylic acid
PUBLISHER: Chiang Mai University

Kanaani, A., Ajloo, D., Kiyani, H., Amri, S.A.N. First-principles study of the electronic transport properties of a 1,3-diazabicyclo[3.1.0]hex-3-ene molecular optical switch (2018) Optik, 153, pp. 135-143.

DOI: 10.1016/j.ijleo.2017.09.125

We analyze the transport properties of 4-(6-(4-chlorophenyl)-4-phenyl-1,3-diaza-bicyclo[3.1.0]hex-3-en-2-yl)-2-nitrophenol molecular optical switch using first-principles calculations. Molecule consisting switch can transform among closed and open forms by visible or ultraviolet irradiation. We have studied multiple attributes such as I–V characteristics, electronic transmission coefficients T(E), the effect of electrode materials (Au, Ag, and Pt) on electronic transport properties, on-off ratio and spatial distribution of molecular projected self-consistent Hamiltonian (MPSH) orbitals corresponding to the closed and open forms. The physical origin of switching behavior is interpreted based on the different molecular geometries, location and size of the frontier molecular orbitals and the HOMO–LUMO gap. According to the theoretical results, one can found that when the open form converts to the closed form, there is a switch from low resistance (on state) to high resistance (off state). We hope that the results of this study can help researchers to design new functional molecular devices. © 2017 Elsevier GmbH

AUTHOR KEYWORDS: Electronic transport; Non-equilibrium green's function; Optical molecular switch
INDEX KEYWORDS: Calculations; Irradiation; Molecular orbitals; Optical switches; Transport properties, Electronic transmission coefficient; Electronic transport; Electronic transport properties; First-principles calculation; Frontier molecular orbitals; Molecular optical switch; Non-equilibrium Green's function; Optical molecular switches, Electric switches
PUBLISHER: Elsevier GmbH

Kiyani, H., Tazari, M. Aqua one-pot, three-component synthesis of dihydropyrano[3,2-c]chromenes and amino-benzochromenes catalyzed by sodium malonate (2017) Research on Chemical Intermediates, 43 (11), pp. 6639-6650.

DOI: 10.1007/s11164-017-3011-7

The widespread biological properties of dihydropyrano[3,2-c]chromenes, 2-amino-4-aryl-4H-benzo[h]chromenes, and 3-amino-1-aryl-1H-benzo[f]chromenes have led to increasing efforts for the development of tremendously effective synthetic protocols aimed at their synthesis. In this contribution, sodium malonate was employed for the first time as an efficient catalyst for the one-pot, three-component tandem Knoevenagel–cyclocondensation reaction of 4-hydroxycoumarin (or naphthols), malononitrile/ethyl cyanoacetate, and various aldehydes. These compounds underwent Knoevenagel–Michael–Thorpe–Ziegler cyclization upon heating at 70 °C in water to give the respective medicinally relevant dihydropyrano[3,2-c]chromenes and amino-benzochromenes. The method is versatile and amenable to many substrates as it requires no specialized devices such as microwave, ultrasound and ball-milling. Also, the salient features of this high-yielding protocol are green reaction conditions, the use of commercially available catalyst, easy purification processes by a simple filtration, and relatively shorter reaction times. © 2017, Springer Science+Business Media B.V.

AUTHOR KEYWORDS: Amino-benzochromene; Dihydropyrano[3,2-c]chromene; Green chemistry; Sodium malonate; Three-component reaction; Water
INDEX KEYWORDS: Ball milling; Catalysts; Water, Amino-benzochromene; Dihydropyrano[3,2-c]chromene; Green chemistry; Sodium malonate; Three component reactions, Sodium
PUBLISHER: Springer Netherlands

Kiyani, H., Darbandi, H. Efficient solvent-free synthesis of 14H-dibenzo[a,j] xanthenes catalyzed by 2-hydroxy-5-sulfobenzoic acid (2017) Chiang Mai Journal of Science, 44 (4), pp. 1504-1511.

DOI: 10.2174/1574884712666170704145046

The use of 2-hydroxy-5-sulfobenzoic acid (2-HSBA) to demonstrate the catalyze one-pot condensation of 2-naphthol with various aldehydes under solvent-free conditions is described. This method can be implemented with a wide variety of readily accessible reagents to provide 14H-dibenzo[a,j]xanthenes as the dye candidates. A significant feature for the present method to the synthesis of 14H-dibenzo[a,j]xanthenes is that the reactions were performed in the absence of solvent and give products in good to high yields. This approach is reasonably priced, and commercially available of the catalyst is also valuable point for the presented procedure. © 2017, Chiang Mai University. All rights reserved.

AUTHOR KEYWORDS: 14H-dibenzo[a,j]xanthene; 2-hydroxy-5-sulfobenzoic acid; 2-naphthol; Condensation; Solventfree
PUBLISHER: Chiang Mai University

Kiyani, H., Darbandi, H. An expeditious and green synthesis of 3,3′-(Arylmethylene)-bis-(4-hydroxycoumarins) catalyzed by 5-sulfosalicylic acid (2017) Chiang Mai Journal of Science, 44 (3), pp. 1002-1010.

The expeditious synthesis of 3,3′-(arylmethylene)-bis-(4-hydroxycoumarins) via a three-component domino Knoevenagel-Michael reaction (3CDKMR) of various aldehydes and 4-hydroxycoumarin, catalyzed by 5-sulfosalicylic acid (SA) is explored. The reactions were conducted at 80 °C using water as a green and environmentally benign medium. The method has several advantages such as reusability of reaction medium, the avoidance of hazardous organic solvents, readily available reagents, cost-effectiveness, and good to high yields. © 2017, Chiang Mai University. All rights reserved.

AUTHOR KEYWORDS: 3,3′-(arylmethylene)-bis-(4-hydroxycoumarins); 4-hydroxycoumarin; 5-sulfosalicylic acid; Three-component reaction; Water
PUBLISHER: Chiang Mai University

Kiyani, H., Samimi, H.A. Nickel-catalyzed one-pot, three-component synthesis of 3,4-disubstituted isoxazole-5(4H)-ones in aqueous medium (2017) Chiang Mai Journal of Science, 44 (3), pp. 1011-1021.

An efficient and simple cyclocondensation approach for the one-pot, three-component synthesis of 3,4-disubstituted isoxazole-5(4H)-ones has been described. This three-component reaction was completed easily and cleanly to give corresponding isoxazoles in the presence of Ni(OAc)2.H2O as the catalyst. The reaction was implemented in aqueous media at room temperature and the corresponding heterocyclic products were obtained in good to high yields. The present work offers notable advantages, including easy work-up, simple procedure, mild condition, and no use of organic solvents. © 2017, Chiang Mai University. All rights reserved.

AUTHOR KEYWORDS: 3,4-disubstituted isoxazole-5(4H)-ones; Ni(OAc)2.H2O; Three-component synthesis; Water; β-oxoesters
PUBLISHER: Chiang Mai University

Banari, H., Kiyani, H., Pourali, A. Efficient synthesis of bis(indolyl)methanes, bispyrazoles and biscoumarins using 4-sulfophthalic acid (2017) Research on Chemical Intermediates, 43 (3), pp. 1635-1649.

DOI: 10.1007/s11164-016-2720-7

4-Sulfophthalic acid (4-H3SPA) solution 50 wt% in H2O has been effectively catalyzed the synthesis of a series of biologically relevant bis(indolyl)methanes by the electrophilic substitution of indole derivatives on aldehyde compounds and 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s by condensing 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one with various aldehydes under aqua conditions at room temperature. 3,3′-(Arylmethylene)-bis-4-hydroxycoumarins have also been synthesized in the presence of 0.1 mL (0.262 mmol) of 4-H3SPA solution 50 wt% in H2O at 80 °C. The procedure is simple and the expected bis-heterocyclic compounds were isolated in good to excellent yields. The present protocol provides the benefits of convenience, mild reaction conditions, eco-friendliness, and no use of hazardous organic solvents. © 2016, Springer Science+Business Media Dordrecht.

AUTHOR KEYWORDS: 4-Hydroxycoumarin; 4-Sulfophthalic acid; 5-Methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one; Bis(indolyl)methanes; Biscoumarins; Bispyrazoles; Indole derivatives
INDEX KEYWORDS: Aldehydes; Polycyclic aromatic hydrocarbons, 4-Hydroxycoumarin; 5-Methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one; Bis(indolyl)methanes; Biscoumarins; Bispyrazoles; Indole derivatives, Methane
PUBLISHER: Springer Netherlands

Kiyani, H., Bamdad, M. One-pot four-component synthesis of 1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles catalyzed by potassium phthalimide (2017) Revue Roumaine de Chimie, 62 (3), pp. 221-226.

The potassium phthalimide (PPI) promoted a domino Knoevenagel-Michael-cyclocondensation of a wide variety of aldehydes, ethyl acetoacetate, malononitrile, and hydrazine derivatives to afford the 1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in high yields. The reactions were performed in refluxing ethanol at shorter reaction times. The significant advantages of this reaction include one-pot process, commercially accessible organocatalyst, simple work-up procedure, reusability of the catalyst, low cost, the use of ethanol as a green solvent, and environmentally friendly solid basic catalyst. (Chemical Equation Presented). © 2017, Editura Academiei Romane. All rights reserved.

PUBLISHER: Editura Academiei Romane

Kiyani, H., Aslanpour, S. Synthesis of Erlenmeyer-Plöchl azlactones promoted by 5-Sulfosalicylic acid (2017) Heterocycles, 94 (7), pp. 1314-1321.

DOI: 10.3987/COM-17-13711

5-Sulfosalicylic acid was found as an efficient catalyst in the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones by condensation and cyclodehydration of aromatic aldehydes with hippuric acid and acetic anhydride at room temperature. The catalyst was easily recycled from the filtrate via evaporation of solvent and reused. This process is green, simple to handle, commercially available starting materials and catalyst, mild conditions, as well as it does not require to hazardous organic solvents, heating, and microwave and ultrasound irradiations. © 2017 The Japan Institute of Heterocyclic Chemistry.

PUBLISHER: Japan Institute of Heterocyclic Chemistry

Kiyani, H., Ghorbani, F. Potassium phthalimide as efficient basic organocatalyst for the synthesis of 3,4-disubstituted isoxazol-5(4H)-ones in aqueous medium (2017) Journal of Saudi Chemical Society, 21, pp. S112-S119.

DOI: 10.1016/j.jscs.2013.11.002

Potassium phthalimide (PPI) is employed as an efficient and effective basic organocatalyst for the one-pot three-component reaction of β-oxoesters with hydroxylamine hydrochloride and various aromatic aldehydes. This cyclocondensation reaction was performed in water as an environmentally benign solvent at room temperature giving 3,4-disubstituted isoxazol-5(4H)-ones in good to excellent yields. PPI was found to be an effective organocatalyst for the synthesis of isoxazol-5(4H)-one system. The advantages of this method are efficiency, clean, easy work-up, high yields, shorter reaction times, inexpensive, and readily available catalyst. © 2013 King Saud University

AUTHOR KEYWORDS: Aryl aldehydes; Isoxazole-5(4H)-ones; Potassium phthalimide; Three-component; Water
PUBLISHER: Elsevier B.V.

Kiyani, H., Bamdad, M. One-pot and efficient synthesis of 5-aminopyrazole-4-carbonitriles catalyzed by potassium phthalimide (2017) Heterocycles, 94 (2), pp. 276-285.

DOI: 10.3987/COM-16-13623

The potassium phthalimide (PPI) has been found to be an efficient, recyclable, inexpensive, commercially available, and easy to handle catalyst for the synthesis of 5-aminopyrazole-4-carbonitriles through the one-pot, three-component reaction of easily available starting reactants involving aldehydes, phenylhydrazine, and malononitrile. This reaction was performed in a mixture of EtOH:H2O as a green reaction media at 50 °C. The catalyst could be recovered easily from the filtrate via evaporation of solvent and reused many times. The present eco-friendly three-component cyclocondensation offers main benefits including, time-saving, mild conditions, minimize the amount of waste, high atom efficiency, avoiding the hazardous organic solvents or catalysts, and the ease of the work-up. © 2017 The Japan Institute of Heterocyclic Chemistry.

PUBLISHER: Japan Institute of Heterocyclic Chemistry

Ramadoss, H., Kiyani, H., Mansoor, S.S. Triphenylphosphine catalysed facile multicomponent synthesis of 2-amino-3-cyano-6-methyl-4-aryl-4H-pyrans (2017) Iranian Journal of Chemistry and Chemical Engineering, 36 (1), pp. 19-26.

Triphenyl phosphine (PPh3), an efficient and reusable catalyst, catalysed the synthesis of 2-amino-3-cyano-6-methyl-4-aryl-4H-pyran-5-ethylcarboxylate derivatives by one-pot condensation of aromatic aldehydes, malononitrile and ethyl acetoacetate in EtOH-H2O (1:1) at reflux conditions. The results show that aromatic aldehydes containing electron-donating groups or electron-withdrawing groups could react smoothly to give the corresponding products in good to excellent yields. Given the increasing levels of interest in green chemistry, the recyclability and reusability of the catalyst have been evaluated. It was also found that triphenyl phosphine can be recycled at least four times without loss of activity. This method has the advantages of high yield, mild reaction conditions, environmentally benign methodology and short reaction time. © 2016, Jihad Danishgahi. All Rights Reserved.

AUTHOR KEYWORDS: Malononitrile; Multicomponent reaction; One-pot synthesis; Pyrans; Triphenyl phosphine
PUBLISHER: Jihad Danishgahi

Kiyani, H., Ghorbani, F. Expeditious green synthesis of 3,4-disubstituted isoxazole-5(4H)-ones catalyzed by nano-MgO (2016) Research on Chemical Intermediates, 42 (9), pp. 6831-6844.

DOI: 10.1007/s11164-016-2498-7

In this work, it was found that magnesium oxide nanoparticles (nano-MgO) catalyzed one-pot three-component reaction of hydroxylamine hydrochloride with aryl aldehydes (or heteroaryl aldehydes) and β-oxoesters to synthesize some biologically active isoxazole-5(4H)-one-based heterocycles. The reactions were completed using 3 mol% catalyst loading in aqueous medium at room temperature. Nano-MgO was synthesized by precipitation and hydrothermal treatment of aqueous salt solution. The structure of the nano-MgO was characterized by X-ray diffraction (XRD) and scanning electron microscopy (SEM) analyses. The presented environmentally friendly heterocyclization offers some interesting merits, including safety, high product yield, mild conditions, low cost, minimal waste, good atom efficiency, catalyst recoverable, energy efficiency, avoidance of hazardous organic solvents, and easy workup. © 2016, Springer Science+Business Media Dordrecht.

AUTHOR KEYWORDS: Isoxazole-5(4H)-ones; Nano-MgO; Three-component reaction; Water; β-Oxoester
INDEX KEYWORDS: Aldehydes; Catalysis; Catalysts; Energy efficiency; Precipitation (chemical); Scanning electron microscopy; Synthesis (chemical); Water; X ray diffraction, Aqueous salt solution; Catalyst loadings; Heterocyclizations; Hydrothermal treatments; Hydroxylamine hydrochloride; Isoxazoles; Magnesium oxide nanoparticles; Three component reactions, Magnesia
PUBLISHER: Springer Netherlands

Kanaani, A., Ajloo, D., Kiyani, H., Shaheri, F., Amiri, M. Synthesis, molecular structure, spectroscopic investigations and computational study of a potential molecular switch of 2-([1,1’-biphenyl]-4-yl)-2-methyl-6-(4-nitrophenyl)-4-phenyl-1,3 diazabicyclo [3.1.0]hex-3-ene (2016) Journal of Chemical Sciences, 128 (8), pp. 1211-1221.

DOI: 10.1007/s12039-016-1118-9

This work presents a combined experimental and theoretical study on a photochromic compound, 2-([1,1’-biphenyl]-4-yl)-2-methyl-6-(4-nitrophenyl)-4-phenyl-1,3 diazabicyclo [3.1.0]hex-3-ene, existing in closed form (‘A’) and open form (‘B’). The spectroscopic properties of the title compound have been investigated by using IR, UV–Vis and 1H NMR techniques. The molecular geometry and spectroscopic data of the title compound have been calculated by using the density functional method (B3LYP) invoking 6-311G(d,p) basis set. UV-Vis spectra of the two forms were recorded. The excitation energies, oscillator strength, etc., were calculated by time-dependent density functional theory (TD-DFT). Furthermore, molecular electrostatic potential map (MEP), frontier molecular orbital analysis (HOMO–LUMO), total density of state (TDOS) and reactivity descriptors were found and discussed. We applied a first-principles computational approach to study a light-sensitive molecular switch. We find that the conductance of the two isomers varies dramatically, which suggests that this system has potential use as a molecular switch. © 2016, Indian Academy of Sciences.

AUTHOR KEYWORDS: DFT; molecular switch; Photochromism; spectroscopy
INDEX KEYWORDS: Computation theory; Computational chemistry; Isomers; Molecular orbitals; Molecular structure; Photochromism; Spectroscopy, Density-functional methods; Frontier molecular orbitals; Light-sensitive molecular switches; Molecular electrostatic potentials; Molecular switches; Reactivity descriptors; Spectroscopic investigations; Time dependent density functional theory, Density functional theory
PUBLISHER: Springer India

Kanaani, A., Ajloo, D., Kiyani, H., Vakili, M., Farahani, M., Amiri, M. Synthesis, spectroscopic investigations, and computational study of 4-((9,10-dioxo-9,10-dihydroanthracen-1-yl)oxy)-3-methoxybenzaldehyde (2016) Optics and Spectroscopy (English translation of Optika i Spektroskopiya), 121 (2), pp. 246-252.

DOI: 10.1134/S0030400X16080038

4-((9,10-dioxo-9,10-dihydroanthracen-1-yl)oxy)-3-methoxybenzaldehyde has been synthesized in an attempt to obtain a new photochromic compound. The optimized molecular structure, mole fractions of title compound in trans and ana forms have been investigated. UV-visible spectra of the compound were also recorded. Upon irradiation with 300 nm light, the camel solid turned orange, in which a visible absorption band was observed at 475 nm. The electronic properties, such as HOMO, LUMO and band gap energies were obtained by the time-dependent DFT (TD-DFT) approach. The predicted nonlinear optical properties of the title compound are much greater than those of urea. Transition structures were calculated by QST3 and IRC methods which yielded the potential energy surface and activation energy. © 2016, Pleiades Publishing, Ltd.

INDEX KEYWORDS: Electronic properties; Energy gap; Nonlinear optics; Optical properties; Photochromism; Potential energy; Quantum chemistry; Urea, Computational studies; Methoxybenzaldehyde; Non-linear optical properties; Photochromic compound; Spectroscopic investigations; Time-dependent DFT; Transition structures; UV-Visible spectra, Activation energy
PUBLISHER: Maik Nauka-Interperiodica Publishing

Kanaani, A., Ajloo, D., Kiyani, H., Ghasemian, H., Vakili, M., Feizabadi, M. Molecular structure, spectroscopic investigations and computational study on the potential molecular switch of (E)-1-(4-(2-hydroxybenzylideneamino)phenyl)ethanone (2016) Molecular Physics, 114 (13), pp. 2081-2097.

DOI: 10.1080/00268976.2016.1178822

This paper presents a combined experimental and theoretical study on an ortho-hydroxy Schiff base compound, (E)-1-(4-(2-hydroxybenzylideneamino)phenyl)ethanone. The spectroscopic and electrochemical properties of the compound were determined using IR, UV–vis and 1H, 13C NMR as well as cyclic voltammetry techniques. The hydrogen bond strength was studied using the spectroscopic results, geometry calculations, topological and NBO analysis. The results showed that the predicted nonlinear optical (NLO) properties of the title compound are much greater than those of urea. Thermodynamic properties in the range from 100 to 505 K were obtained. Furthermore, molecular electrostatic potential, Fukui functions, thermodynamic, frontier molecular orbital analysis, reactivity descriptors and NLO properties were found and discussed. Theoretical results show that the conductance of the two tautomers varies seriously, which offers that this molecule has potential usage as a molecular device. © 2016 Informa UK Limited, trading as Taylor & Francis Group.

AUTHOR KEYWORDS: molecular switch; Schiff base; spectroscopic investigation; tautomerism
INDEX KEYWORDS: Computational chemistry; Cyclic voltammetry; Hydrogen bonds; Molecular orbitals; Urea, Frontier molecular orbitals; Molecular electrostatic potentials; Molecular switches; Nonlinear optical properties; Reactivity descriptors; Schiff-base; Spectroscopic investigations; tautomerism, Spectroscopic analysis
PUBLISHER: Taylor and Francis Ltd.

Kiyani, H., Jalali, M.S. Facial and efficient access to dihydropyrano[3,2-c]chromenes via three- component reaction using n,n-dimethylbenzylamine as a new organocatalyst (2016) Combinatorial Chemistry and High Throughput Screening, 19 (4), pp. 275-282.

DOI: 10.2174/1386207319666160310144315

The N,N-dimethylbenzylamine (DMBA), as an efficient and commercially available organocatalyst was employed for the one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives in ethanol medium. In this work, the one-pot Knoevenagel-Michael-Thorpe-Ziegler type cascade heterocyclization has been developed for the synthesis of dihydropyrano[3,2-c]chromene-containing heterocycles from the one-pot multicomponent condensation reaction of 4-hydroxycoumarin, malononitrile/ethyl cyanoacetate, and various aldehydes at 60°C. The salient features of this basecatalyzed reaction are mild reaction conditions, reusability of the reaction medium, shorter reaction times, and easy separation of the reaction mixture. © 2016 Bentham Science Publishers.
AUTHOR KEYWORDS: 4-Hydroxycoumarin; Dihydropyrano[3,2-c]chromenes; Knoevenagel condensation; N,N-Dimethylbenzylamine; Nitrile-containing compounds; Three-component annulation

INDEX KEYWORDS: benzylamine derivative; chromene derivative; 4 hydroxycoumarin derivative; 4-hydroxycoumarin; acetic acid derivative; aldehyde; benzopyran derivative; benzylamine derivative; chromone derivative; dicyanmethane; dihydropyranochromone; ethyl cyanoacetate; N-benzyl-N,N-dimethylamine; nitrile, Article; carbon nuclear magnetic resonance; catalyst; chemical reaction; comparative study; Knoevenagel condensation; melting point; one pot synthesis; polymerization; priority journal; proton nuclear magnetic resonance; proton transport; reaction time; three component reaction; catalysis; chemistry; cyclization; synthesis, 4-Hydroxycoumarins; Acetates; Aldehydes; Benzopyrans; Benzylamines; Catalysis; Chromones; Cyclization; Nitriles
PUBLISHER: Bentham Science Publishers B.V.

Kiyani, H., Jalali, M.S. Facile and efficient access to tetrahydrobenzo[b]-pyrans catalyzed by N,N-dimethylbenzylamine (2016) Heterocycles, 92 (1), pp. 75-85.

DOI: 10.3987/COM-15-13360

The N,N-dimethylbenzylamine (DMBA) has been used as an efficient, inexpensive, and commercially available organocatalyst for the one-pot, three-component synthesis of tetrahydrobenzo[b]pyrans in good to high yields. It was found that the one-pot Knoevenagel-Michael-Thorpe-Ziegler cyclization sequence of dimedone, malononitrile/ethyl cyanoacetate, and various aldehydes was efficiently implemented in ethanol at 45 °C. This procedure offers attractive several features: mild reaction conditions, use of ethanol as a green solvent, reusability the reaction media, shorter reaction times, and the ease of the work-up. © 2016 The Japan Institute of Heterocyclic Chemistry.

PUBLISHER: Japan Institute of Heterocyclic Chemistry

Kiyani, H., Ghorbani, F. Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water (2015) Research on Chemical Intermediates, 41 (10), pp. 7847-7882.

DOI: 10.1007/s11164-014-1863-7

A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up. © 2014 Springer Science+Business Media Dordrecht.

AUTHOR KEYWORDS: 4H-Chromenes; 4H-Pyrans; Cyano compounds; Isoxazol-5(4H)-ones; Potassium hydrogen phthalate; Three-component reaction
INDEX KEYWORDS: Carboxylation; Catalysts; Cyanides; Esters; Hydrogen; Potassium; Potassium compounds; Unsaturated compounds, 4H-Pyrans; Chromenes; Cyano compounds; Isoxazol-5(4H)-ones; Potassium hydrogen phthalate; Three component reactions, Synthesis (chemical)
PUBLISHER: Kluwer Academic Publishers

Kiyani, H., Darbandi, H., Mosallanezhad, A., Ghorbani, F. 2-Hydroxy-5-sulfobenzoic acid: An efficient organocatalyst for the three-component synthesis of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones (2015) Research on Chemical Intermediates, 41 (10), pp. 7561-7579.

DOI: 10.1007/s11164-014-1844-x

2-Hydroxy-5-sulfobenzoic acid (2-HSBA) efficiently catalyzed the one-pot three-component synthesis of a wide variety of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones. The three-component process of substituted benzaldehydes, 2-naphthol, and amides (benzamide and acetamide) or urea occur using 10 mol% of 2-HSBA as an organocatalyst under solvent-free reaction conditions (SFRCs) at 100 °C. It was also found that the best results for the preparation of 3,4-disubstituted isoxazol-5(4H)-ones were achieved using 15 mol% of 2-HSBA under aqueous conditions at room temperature. The reactions are easy to do and were completed within 3-25 min (for amidoalkyl naphthols), and 70-120 min (for 3,4-disubstituted isoxazol-5(4H)-ones), while the expected products were obtained in 82-97 % yields. The catalyst can be recovered and reused several times in the template reactions. This procedure offers the advantages of convenience, simple operational procedure, cost-effectiveness, no use of hazardous organic solvents, and the commercial availability of the catalyst. © 2014 Springer Science+Business Media Dordrecht.

AUTHOR KEYWORDS: 1-Amidoalkyl-2-naphthols; 2-Hydroxy-5-sulfobenzoic acid; 3,4-disubstituted isoxazol-5(4H)-ones; Solvent-free; Three-component reaction; Water
INDEX KEYWORDS: Amides; Cost effectiveness; Naphthol; Solvents; Synthesis (chemical); Urea; Water, 1-Amidoalkyl-2-naphthols; 3,4-disubstituted isoxazol-5(4H)-ones; Commercial availability; Operational procedures; Solvent free; Solvent-free reaction conditions; Substituted benzaldehydes; Three component reactions, Catalysts
PUBLISHER: Kluwer Academic Publishers

Kiyani, H., Kanaani, A., Ajloo, D., Ghorbani, F., Vakili, M. N-bromosuccinimide (NBS)-promoted, three-component synthesis of α,β-unsaturated isoxazol-5(4H)-ones, and spectroscopic investigation and computational study of 3-methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one (2015) Research on Chemical Intermediates, 41 (10), pp. 7739-7773.

DOI: 10.1007/s11164-014-1857-5

A three-component, NBS-promoted synthesis of α,β-unsaturated isoxazol-5(4H)-ones by reaction of aromatic aryl or hetero-aryl aldehydes, hydroxylamine hydrochloride, and 1,3-dicarbonyl compounds (ethyl acetoacetate or ethyl 4-chloroacetoacetate), under mild reaction conditions at room temperature is described. This simple, efficient, and clean reaction is an expeditious means of obtaining the corresponding isoxazol-5(4H)-one derivatives in good to high yields. Geometrical properties and vibrational wavenumbers of 3-methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one (MTISO) were predicted by use of density functional theory (DFT) by use of the B3LYP level with the 6-311++G(d,p) and 6-311++G(2d,p) basis sets. Results indicate that the B3LYP method enables satisfactory prediction of vibrational frequencies and structural data. The absorption spectra of MTISO in solvents of different polarity were studied at room temperature. The UV-visible spectrum of the compound was recorded and such electronic properties as the energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) were determined by the time-dependent DFT (TD-DFT) approach. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization was studied by NBO analysis. A molecular electrostatic potential map (MEP) of the compound was also studied to predict reactive sites. Reactivity descriptors, Fukui functions, and electrophilic sites were found and are discussed. The thermal stability of MTISO was studied by thermogravimetric analysis (TGA). © 2014 Springer Science+Business Media Dordrecht.

AUTHOR KEYWORDS: 3-Methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one; DFT; Fukui function; Isoxazol-5(4H)-ones; NBO analysis; NMR and UV spectra
INDEX KEYWORDS: Computation theory; Density functional theory; Electronic properties; Molecular orbitals; Synthesis (chemical); Thermodynamic stability; Ultraviolet spectroscopy; Unsaturated compounds, 3-Methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one; DFT; Fukui functions; Isoxazol-5(4H)-ones; NBO analysis; Nmr and uv spectrum, Thermogravimetric analysis
PUBLISHER: Kluwer Academic Publishers

Kiyani, H., Ghiasi, M. Phthalimide-N-sulfonic acid: a new and efficient organocatalyst for the Biginelli reaction under solvent-free conditions (2015) Research on Chemical Intermediates, 41 (9), art. no. 1766, pp. 6635-6648.

DOI: 10.1007/s11164-014-1766-7

Abstract Phthalimide-N-sulfonic acid (PISA) was straightforwardly synthesized via addition of chlorosulfonic acid to a solution of potassium phthalimide in dry dichloromethane. This reagent is found to be an efficient solid acidic catalyst in the Biginelli reaction. The three-component reaction of aryl aldehydes, urea/thiourea, and ethyl acetoacetate or acetylacetone occurs by means of 10 mol % of PISA in solvent-free reaction conditions (SFRCs) at 120 C. The present methodology is a green approach to access a series of 3,4-dihydropyrimidin-2(1H)-ones/thiones in high yields. In addition, the use of PISA as the catalyst offers several notable features such as simple operational procedure, no use of hazardous organic solvents, and recyclability of catalyst. © 2014 Springer Science+Business Media Dordrecht.

AUTHOR KEYWORDS: 3,4-Dihydropyrimidin-2(1H)-ones/thiones; Biginelli-3CR; Organocatalyst; Phthalimide-N-sulfonic acid; Solvent-free conditions
INDEX KEYWORDS: Acetone; Chemical reactions; Dichloromethane; Solvents; Urea, 3,4-Dihydropyrimidin-2(1H)-ones/thiones; Biginelli; Organocatalysts; Solvent free conditions; Sulfonic acid, Catalysts
PUBLISHER: Kluwer Academic Publishers

Kanaani, A., Ajloo, D., Ghasemian, H., Kiyani, H., Vakili, M., Mosallanezhad, A. Synthesis, molecular structure, spectroscopic investigations and computational studies of (E)-1-(4-(4-(diethylamino)-2-hydroxybenzylideneamino)phenyl)ethanone (2015) Structural Chemistry, 26 (4), art. no. 571, pp. 1095-1113.

DOI: 10.1007/s11224-015-0571-2

Abstract The Schiff base compound (E)-1-(4-(4-(diethylamino)-2-hydroxybenzylideneamino)phenyl)ethanone has been synthesized and characterized by IR, UV-Vis, and 1H and 13C NMR techniques. These properties of title compound were also investigated from calculative point of view. UV-Vis spectra of the title compound were recorded in different organic solvents to investigate the dependence of tautomerism on solvent types. Calculated results reveal that its enol form is more stable than its keto form. A detailed analysis of the nature of the hydrogen bonding, using topological parameters, evaluated at bond critical points. © 2015 Springer Science+Business Media New York.

AUTHOR KEYWORDS: DFT; Intramolecular proton transfer; Schiff base; Spectroscopy
PUBLISHER: Springer New York LLC

Kiyani, H., Ghiasi, M. Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst (2015) Research on Chemical Intermediates, 41 (8), pp. 5177-5203.

DOI: 10.1007/s11164-014-1621-x

The usage of potassium phthalimide (PPI) for the simple and green one-step multicomponent synthesis of Hantzsch 1,4-dihydropyridines, polyhydroquinolines, 3,4-dihydropyrimidin-2(1H)-ones/thiones, and octahydroquinazolinones under solventless conditions at 120°C is reported. The method is operationally simple, environmentally benign, and has relatively high yields. The other merits of this method include efficient, clean, green, and catalyst reusability. © Springer Science+Business Media Dordrecht 2014.

AUTHOR KEYWORDS: 1,4-Dihydropyridines; 3,4-Dihydropyrimidin-2(1H)-ones/thiones; Octahydroquinazolinones; Polyhydroquinolines; Potassium phthalimide; Solventless conditions
INDEX KEYWORDS: Catalysts; Potassium; Reusability, 1 ,4-Dihydropyridines; 3,4-Dihydropyrimidin-2(1H)-ones/thiones; Octahydroquinazolinones; Polyhydroquinolines; Potassium phthalimide; Solventless, Potassium compounds
PUBLISHER: Kluwer Academic Publishers

Kiyani, H., Albooyeh, F., Fallahnezhad, S. Synthesis of new pyrazolyl-1,3-diazabicyclo[3.1.0]hexe-3-ene derivatives (2015) Journal of Molecular Structure, 1091, pp. 163-169.

DOI: 10.1016/j.molstruc.2015.02.069

A series of new of photochromic 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives based on the skeleton of five-membered pyrazole moiety have been synthesized and characterized by spectral techniques, as well as their photochromic properties were examined under UV light irradiation in various solutions. All these newly synthesized compounds showed good photochromic properties in the both solution and solid states. The UV-Visible spectral analysis of the corresponding pyrazolyl bicyclic aziridines established structure-photochromic behavior relationships. © 2015 Elsevier B.V. All rights reserved.

AUTHOR KEYWORDS: 1,3-Diazabicyclo[3.1.0]hex-3-ene; Bicyclic aziridine; Photochromic; Pyrazole carbaldehyde; Vielsmeier-Haack reaction
INDEX KEYWORDS: Ionic liquids; Organic compounds; Spectrum analysis; Synthesis (chemical), 1,3-Diazabicyclo[3.1.0]hex-3-ene; Aziridines; Photochromic; Pyrazoles; Vielsmeier-Haack reaction, Photochromism
PUBLISHER: Elsevier

Kiyani, H., Ghorbani, F. Potassium phthalimide: An efficient and simple organocatalyst for the one-pot synthesis of dihydropyrano[3,2-c]chromenes in aqueous media (2015) Research on Chemical Intermediates, 41 (6), pp. 4031-4046.

DOI: 10.1007/s11164-013-1508-2

A series of dihydropyrano[3,2-c]chromene derivatives were obtained via treating cyano methylene compounds (malononitrile or ethyl cyanoacetate), aromatic aldehydes, and 4-hydroxycoumarin in the presence of potassium phthalimide, as a green, mild, efficient, and commercially available organocatalyst in aqueous media. This procedure was easily performed, which provides a straightforward route for the synthesis of diverse dihydropyrano[3,2-c]chromene compounds. Safety, short reaction times, environmentally friendly, no use of hazardous organic solvents, and high yields are remarkable advantages of this process. © 2013 Springer Science+Business Media Dordrecht.

AUTHOR KEYWORDS: Cyano compounds; Dihydropyrano[3,2-c]chromenes; Potassium phthalimide; Three-component process
INDEX KEYWORDS: Catalysts; Potassium, Chromene derivatives; Chromenes; Cyano compounds; Ethyl cyanoacetate; Methylene compounds; Potassium phthalimide; Short reaction time; Three component, Potassium compounds
PUBLISHER: Kluwer Academic Publishers

Kiyani, H., Ghorbani, F. Boric acid-catalyzed multi-component reaction for efficient synthesis of 4H-isoxazol-5-ones in aqueous medium (2015) Research on Chemical Intermediates, 41 (5), art. no. 1411, pp. 2653-2664.

DOI: 10.1007/s11164-013-1411-x

Abstract The one-pot three-component reaction of aryl aldehydes with hydroxylamine hydrochloride and ethyl 3-oxobutanoate/ethyl 4-chloro-3-oxobutanoate/ethyl 3-oxo-3-phenylpropanoate in the presence of boric acid, H3BO3, in water leads to 4H-isoxazol-5(4H)-ones in high yields. The merits of this method are efficiency, simplicity, clean, green, easy work-up, high yields, and shorter reaction times. © Springer Science+Business Media Dordrecht 2013.
AUTHOR KEYWORDS: Boric acid; Green; Isoxazol; Three-component reaction
INDEX KEYWORDS: Boride coatings; Synthesis (chemical), Aqueous medium; Aryl aldehydes; Efficient synthesis; Green; Hydroxylamine hydrochloride; Isoxazol; Multi-component reactions; Three component reactions, Boric acid
PUBLISHER: Kluwer Academic Publishers

Kiyani, H., Daroonkala, M.D. A cost-effective and green aqueous synthesis of 3-substituted coumarins catalyzed by potassium phthalimide (2015) Bulletin of the Chemical Society of Ethiopia, 29 (3), pp. 449-456.

DOI: 10.4314/bcse.v29i3.13

An efficient procedure for the synthesis of various 2-imino-2H-chromene-3-carbonitriles, 2-oxo- 2H-chromene-3-carbonitriles as well as 2-oxo-2H-chromene-3-carboxylic acids is reported. It has been found that potassium phthalimide (PPI) catalyse the Knoevenagel condensation reaction of salicylaldehydes and activated β- dicarbonyl compounds efficiently under aqueous conditions at room temperature. This approach provides many merits such as high yields of products, clean, simple work-up, waste free, mild reaction conditions, commercially available organocatalyst, and the use of water as environmentally benign solvent. © 2015 Chemical Society of Ethiopia.


AUTHOR KEYWORDS: 2-Imino-2H-coumarin-3-carbonitrile; 2-Oxo-2H-chromene-3-carboxylic acid; 2-Oxo-2Hchromene- 3-carbonitrile; Potassium phthalimide; Salicylaldehydes
PUBLISHER: Chemical Society of Ethiopia

Kiyani, H., Fallahnezhad, S., Albooyeh, F. Synthesis of new ferrocenyl 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives (2015) Letters in Organic Chemistry, 12 (3), pp. 168-175.

DOI: 10.2174/1570178612666150108001015

In this work, several new derivatives of ferrocenyl bicylic aziridine photochromic compounds have been prepared from the premade ketoaziridines and ferrocene carboxaldehyde in the presence of ammonium acetate in absolute ethanol via one-pot, three-component reaction. The structures of the newly synthesized compounds were established on the basis of IR, NMR and UV-Vis spectral studies. The newly synthesized compounds exhibit interesting photochromic behavior in the solid phase and solution state. The photochromic behavior of the prepared compounds has been investigated by UV-Visible spectral data. © 2015 Bentham Science Publishers.


AUTHOR KEYWORDS: 1,3-Diazabicyclo[3.1.0]hex-3-ene; Ferrocene; Ketoaziridine; Photochromism
PUBLISHER: Bentham Science Publishers B.V.

Shiran, J.A., Yahyazadeh, A., Yamin, B.M., Mamaghani, M., Kiyani, H. Three-component synthesis of new substituted bis[2-imino-3-(substituted)-4-phenyl-3h-thiazole] derivatives and evaluation of their antibacterial activity (2015) Heterocycles, 91 (1), pp. 123-133.

DOI: 10.3987/COM-14-13123

Several new derivatives of 2,2′-(4,4′-ethylenebiphenyl)bis[2-imino-3-(substituted)-4-phenyl-3H-thiazole],2,2′-(4,4′-biphenylsulfone)bis[2-imino-3-(substituted)-4-phenyl-3H-thiazole],2,2′-(4,4′-methylenebiphenyl)bis[2-imino-3-(substituted)-4-phenyl-3H-thiazole] and 2,2′-(1,4-phenylene)bis[2-imino-3-(substituted)-4-phenyl-3H-thiazole] derivatives were synthesized by the condensation reaction of various isothiocyanates, diamines, and phenacyl bromide. The one-pot, three-component synthesis of new iminothiazole-containing heterocyles were conducted using catalytic amounts of triethylamine. Furthermore, the target compound 8b was further determined by X-ray crystallographic analysis. The antimicrobial activity of the synthesized compounds was evaluated against Salmonella enterica, Micrococcus luteus, Bacillus subtilis and Pseudomonas aeruginosa. © 2015 The Japan Institute of Heterocyclic Chemistry.

PUBLISHER: Japan Institute of Heterocyclic Chemistry

Kanaani, A., Ajloo, D., Kiyani, H., Farahani, M. Synthesis, spectroscopic investigations and computational study of 4-((9,10-dioxo-9,10-dihydroanthracen-1-yl)oxy)benzaldehyde (2014) Journal of Molecular Structure, 1063 (1), pp. 30-44.

DOI: 10.1016/j.molstruc.2014.01.040

The molecular structure, vibrational frequencies, corresponding vibrational assignments of 4-((9,10-dioxo-9,10-dihydroanthracen-1-yl)oxy)benzaldehyde in "trans" and "ana" forms have been investigated by UV-Vis, FT-IR and NMR spectroscopy as well as density functional theory (DFT) B3LYP method with 6-311++G(d,p) basis set. The vibrational analysis of the two forms of cited compound was performed by means of infrared absorption spectroscopy in combination with theoretical simulations. The obtained geometrical parameters and wavenumbers of vibrational normal modes from the DFT method were in good consistency with the experimental values. The 1H and 13C nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by GIAO method. Computed molecular orbital and time dependent DFT oscillator renderings agree closely with experimental observations. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. In order to predict the reactive sites, a molecular electrostatic potential map (MEP) for the title compound was obtained. Transition structures were calculated by QST3 and IRC methods which yielded the potential energy surface and activation energy. © 2014 Elsevier B.V. All rights reserved.

AUTHOR KEYWORDS: Density functional theory; NBO; Photochromism; QST3; Spectroscopy

Kiyani, H., Ghiasi, M. Potassium phthalimide: An efficient and green organocatalyst for the synthesis of 4-aryl-7-(arylmethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d] pyrimidin-2(5H)-ones/thiones under solvent-free conditions (2014) Chinese Chemical Letters, 25 (2), pp. 313-316.

DOI: 10.1016/j.cclet.2013.11.042

An efficient synthesis of Biginelli-type compounds using potassium phthalimide as a green, mild, and commercially available organocatalyst in a one-pot, multi-component cyclocondensation reaction of cyclopentanone, aldehydes, and urea/thiourea is reported. The present methodology is a green approach to access 4-aryl-7-(arylmethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d] pyrimidin-2(5H)-ones/thiones. It offers several merits such as simple operational procedures, no use of hazardous organic solvents, and cheap and environmentally friendly solid basic catalyst. © 2013 Hamzeh Kiyani. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

AUTHOR KEYWORDS: Biginelli reaction; Organocatalyst; Potassium phthalimide; Pyrimidinone; Solvent-free

Kiyani, H., Ghorbani, F. Potassium phthalimide promoted green multicomponent tandem synthesis of 2-amino-4H-chromenes and 6-amino-4H-pyran-3-carboxylates (2014) Journal of Saudi Chemical Society, 18 (5), pp. 689-701.

DOI: 10.1016/j.jscs.2014.02.004

A one-pot efficient, green, practical, and environmentally friendly multicomponent synthesis of 5-oxo-4-aryl-5,6,7,8-tetrahydro-4. H-chromenes, ethyl-6-amino-4-aryl-5-cyano-2-methyl-4. H-pyran-3-carboxylates as well as 2-amino-4-aryl-7-hydroxy-4. H-chromene-3-carbonitriles via tandem the Knoevenagel-cyclocondensation has been described in the presence of a green, low-cost, mild, efficient, and commercially available potassium phthalimide as the organocatalyst. This technique is a safe and ecofriendly approach to the synthesis of different 4. H-chromens and 4. H-pyrans that offers many merits including short reaction times, high yields, straightforward work-up, and no use of hazardous organic solvents. © 2014 King Saud University.

AUTHOR KEYWORDS: 4H-Chromene; 4H-Pyran-3-carboxylate; Multicomponent process; Potassium phthalimide
PUBLISHER: Elsevier

Kiyani, H., Ghorbani, F. Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media (2014) Chemical Papers, 68 (8), pp. 1104-1112.

DOI: 10.2478/s11696-014-0554-6

2-Amino-4-aryl-4H-benzo[h]chromenes and 3-amino-1-aryl-1H-benzo[f]chromenes were prepared by treating cyano-methylene compounds (malononitrile or ethyl cyanoacetate), substituted aromatic aldehydes, and naphtholic compounds in the presence of potassium phthalimide as a green, mild, efficient, and commercially available organocatalyst in aqueous media. The procedure was readily conducted and affords remarkable advantages such as safety, short reaction times, environmentally benign milder reaction conditions, no organic solvent required, and high yields. © 2014 Institute of Chemistry, Slovak Academy of Sciences.

AUTHOR KEYWORDS: amino-benzochromene; nitrile compounds; potassium phthalimide; three-component process
PUBLISHER: Versita

Albooye, F., Kiyani, H. 2-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophen-yl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene (2013) MolBank, 2013 (3), .

DOI: 10.3390/M806

As a consequence of one-pot, three-component reaction of trans-2-benzoyl-3- (4-nitrophenyl)aziridine with 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and ammonium acetate, 2-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene was achieved in good yield. The desired photochromic compound display interesting photochromic behavior in the crystalline and solution phase. The structure of the newly synthesized photochromic compound was characterized by elemental analysis, 1H-NMR, 13C-NMR and UV-Visible spectral data. © 2013 by the author; licensee MDPI, Basel, Switzerland.

AUTHOR KEYWORDS: Bicyclic aziridine; Photochromism; Pyrazole; Vilsmeier-haack reaction

Samimi, H.A., Kiyani, H., Shams, Z. Stereo-controlled deamination of ketoaziridines using Ph3P, I2 (2013) Journal of Chemical Research, 37 (5), pp. 282-284.

DOI: 10.3184/174751913X13646666428217

Ph3P, I2is an efficient reagent for the stereo-controlled deamination of non-activated aziridines, N-H and N-alkyl aziridines, using. The method works gives the corresponding trans-alkenes from both cis and trans-aziridines. A plausible mechanism is proposed for the ring opening and deamination of keto-aziridines in the presence of Ph3P, I2.

AUTHOR KEYWORDS: Deamination; I2; Ketoaziridine; Non-activated aziridine; Ph 3P; Ring opening

Kiyani, H., Ardyanian, M. N-(4-(6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3- ene-2-yl)phenyl)acetamide (2012) MolBank, 2013 (1), .

DOI: 10.3390/M791

As a result of three-component one-pot reaction of trans-2-benzoyl-3-(4- nitrophenyl)aziridine with 4-acetamidobenzaldehyde and ammonium acetate, N-(4-(6-(4- nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene-2-yl)phenyl)acetamide was obtained in good yield. The newly synthesized compound exhibit interesting photochromic behavior in the solid and solution state. The structure of the synthesized compound was confirmed by elemental analysis, 1H-NMR, 13C-NMR and UV-Visible spectral data. © 2013 by the authors; licensee MDPI, Basel, Switzerland.

AUTHOR KEYWORDS: 4-acetamidobenzaldehyde; Diazabicyclo[3.1.0]hex-3-ene; Photochromism

Kiyani, H. 2-(4-Diethoxymethylphenyl)-6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene (2012) MolBank, 2012 (4), .

DOI: 10.3390/M780

The photochromic compound was obtained from 4-diethoxymethyl-benzaldehyde and trans-2-benzoyl-3-(4-nitrophenyl)aziridine via a three component reaction. The structure of this compound was characterized by elemental analysis, 1H-NMR, 13C-NMR and UV-Visible spectral data. © 2012 by the author; licensee MDPI, Basel, Switzerland.

AUTHOR KEYWORDS: 4-diethoxymethylbenzaldehyde; Bicyclic aziridine; Photochromism

Mahmoodi, N.O., Tabatabaeian, K., Kiyani, H. Two 1,3-Diazabicyclo[3.1.0]hex-3-enes with a 'Tripod' core (2012) Helvetica Chimica Acta, 95 (3), pp. 536-542.

DOI: 10.1002/hlca.201100333

The photochromic 1,3-diazabiclyclo[3.1.0]hex-3-enes 5 and 6 were synthesized from two premade tris-aldehydes and two premade aziridinyl ketones and characterized (Scheme 1). Their spectra showed structurei-photochromic behavior relationships (SPBR), which were analyzed. Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.

AUTHOR KEYWORDS: 'Tripod' core; 1,3-Diazabicyclo[3.1.0]hex-3-ene; Photochromism; Structurei-photochromic behavior relationship (SPBR)
INDEX KEYWORDS: 'Tripod' core; 1,3-Diazabicyclo[3.1.0]hex-3-ene; Structurei-photochromic behavior relationship (SPBR), Aldehydes; Ketones; Organic compounds, Photochromism, 1,3 diazabicyclo[3.1.0]hex 3 ene derivative; bicyclo compound; unclassified drug, absorption spectroscopy; article; chemical analysis; crystal structure; photochemistry; priority journal; structure activity relation; synthesis

Mahmoodi, N.O., Asadollahi, E., Kiyani, H., Naseri, N. Synthesis and photochromism of quinolines and benzo[h]quinolines of 1,3-diazabicyclo[3.1.0]hex-3-ene (2011) International Journal of Photoenergy, 2011, art. no. 218427, .

DOI: 10.1155/2011/218427

1,3-Diazabicyclo[3.1.0]hex-3-ene systems represent a very interesting class of organic materials, possessing unique photochromic properties in the solid state. It has been demonstrated that these compounds form deeply colored, fairly stable materials under UV radiation. Here, for the first time we report synthesis of several 1,3-diazabicyclo[3.1.0]hex-3-enes with premade substituted quinoline and benzo[h]quinoline rings. Copyright © 2011 Nosrat O. Mahmoodi et al.

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