Glutamic Acid as an Environmentally Friendly Catalyst for One-Pot Synthesis of 4H-Chromene Derivatives and Biological Activity

In this study, the synthesis of 4 H -chromenes of biological activity via a multicomponent reaction of dimedone, aromatic aldehydes and malononitrile catalyzed by glutamic acid as a catalyst was investigated. The structural features of the synthesized compounds were characterized by melting point, IR and 1 H NMR analysis. The catalyst being reported here is cheap, safe to handle and the whole procedure is eco-friendly, Milder conditions, one-pot, excellent yields, operational simplicity and ecofriendly preparation are some advantages of this protocol. The compounds were screened for antimicrobial activity. The results showed that these compounds reacted against all the tested bacteria and fungi.

[1]  M. Khavarpour,et al.  A Facile and Highly Efficient Three Component Synthesis of Pyran and Chromene Derivatives in the Presence of Nano SnO2 as a catalyst , 2015 .

[2]  F. Hatamjafari,et al.  Synthesis of Coumarin Derivatives using Glutamic Acid under Solvent-free Conditions , 2014 .

[3]  F. Hatamjafari.  Biological Activity and Efficient Synthesis of 3, 4- Dihydropyrimidin-2-(1H)-one/thione Derivatives , 2014 .

[4]  E. Abbasi,et al.  Glutamic acid as an Efficient Catalyst for Synthesis of Dihydropyrimidinones , 2013 .

[5]  A. Maleki,et al.  Potassium phthalimide-N-oxyl: a novel, efficient, and simple organocatalyst for the one-pot three-component synthesis of various 2-amino-4H-chromene derivatives in water , 2013 .

[6]  M. Tajbakhsh,et al.  Well-Ordered Mesoporous Silica Nanoparticles as a Recoverable Catalyst for One-Pot Multicomponent Synthesis of 4H-Chromene Derivatives , 2012 .

[7]  S. Allameh,et al.  One-pot synthesis of 2-amino-3-cyano-4-arylsubstituted tetrahydrobenzo[b]pyrans catalysed by silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst , 2011 .

[8]  N. Karimi,et al.  Caro's Acid–Silica Gel: An Efficient and Versatile Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives , 2011 .

[9]  Yiqun Li,et al.  One-pot synthesis of tetrahydrobenzo[b]pyran and dihydropyrano[c]chromene derivatives in aqueous media by using trisodium citrate as a green catalyst , 2011 .

[10]  Guigen Li,et al.  New multicomponent domino reactions (MDRs) in water: highly chemo-, regio- and stereoselective synthesis of spiro{[1,3]dioxanopyridine}-4,6-diones and pyrazolo[3,4-b]pyridines , 2010 .

[11]  B. Trofimov,et al.  C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction. , 2010 .

[12]  Peng Zhang,et al.  Lithium Bromide as a Mild, Efficient, and Recyclable Catalyst for the One-Pot Synthesis of Tetrahydro-4H-Chromene Derivatives in Aqueous Media , 2010 .

[13]  De‐Xian Wang,et al.  Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes. , 2009, The Journal of organic chemistry.

[14]  S. Kapur,et al.  A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. , 2009, European journal of medicinal chemistry.

[15]  K. A. Undale,et al.  Potassium Phosphate Catalyzed a Rapid Three-Component Synthesis of Tetrahydrobenzo[b]pyran at Ambient Temperature , 2009 .

[16]  R. Raja,et al.  Single-site Biomimetic Amino Acid Complexes for the Benign Oxidation of Hydrocarbons and Alcohols , 2009 .

[17]  G. Sabitha,et al.  Cerium(III) Chloride–Catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]pyrans , 2009 .

[18]  H. Sheibani,et al.  High Surface Area MgO as a Highly Effective Heterogeneous Base Catalyst for Three-Component Synthesis of Tetrahydrobenzopyran and 3,4-Dihydropyrano[c]chromene Derivatives in Aqueous Media , 2008 .

[19]  A. A. El-kateb,et al.  Simplified Approach to the Uncatalyzed Knoevenagel Condensation and Michael Addition Reactions in Water Using Microwave Irradiation. , 2008 .

[20]  S. Majedi,et al.  Sodium selenate catalyzed simple and efficient synthesis of tetrahydro benzo[b]pyran derivatives , 2008 .

[21]  Ji-tai Li,et al.  D,L‐Proline‐Catalyzed One‐Pot Synthesis of Pyrans and Pyrano[2,3‐c]pyrazole Derivatives by a Grinding Method under Solvent‐Free Conditions , 2007 .

[22]  F. Hatamjafari.  New Protocol to Synthesize Spiro‐1,4‐dihydropyridines by Using a Multicomponent Reaction of Cyclohexanone, Ethyl Cyanoacetate, Isatin, and Primary Amines under Microwave Irradiation. , 2007 .

[23]  A. Karimi,et al.  Multi-Component Reaction of Amines, Alkyl Propiolates, and Ninhydrin: An Efficient Protocol for the Synthesis of Tetrahydro-dihydroxy-oxoindeno[1,2-b]pyrrole Derivatives. , 2006 .

[24]  J. Azizian,et al.  One-pot rapid and efficient synthesis of new spiro derivatives of 11H-indeno(1,2-b)quinoxalin-11-one, 6H-indeno(1,2-b)pyrido (3,2-e)pyrazin-6-one and isatin-based 2-pyrazolines , 2006 .

[25]  A. Amani,et al.  (S)-Proline as a Neutral and Efficient Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives in Aqueous Media , 2006 .

[26]  P. Bhuyan,et al.  Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions , 2004 .

[27]  Ji-tai Li,et al.  One‐Pot Synthesis of 2‐Amino‐4‐aryl‐3‐carbalkoxy‐7,7‐dimethyl‐5,6,7,8‐tetrahydrobenzo[b]pyran Derivatives Catalyzed by KF/Basic Al2O3 Under Ultrasound Irradiation , 2004 .

[28]  P. Reddanna,et al.  Lipoxygenase Metabolites of α-linolenic Acid in the Development of Resistance in Pigeonpea, Cajanus cajan (L.) Millsp, Seedlings Against Fusarium udum Infection , 2000, European Journal of Plant Pathology.

[29]  D. Shi,et al.  A CONVENIENT SYNTHESIS OF 2-AMINO-5,6,7,8-TETRAHYDRO-5-OXO- 4-ARYL-7,7-DIMETHYL-4H-BENZO-[b]-PYRAN-3-CARBONITRILE UNDER MICROWAVE IRRADIATION , 2002 .

[30]  C. Kappe.  Recent Advances in the Biginelli Dihydropyrimidine Synthesis. New Tricks from an Old Dog , 2001 .

[31]  M. C. Martínez,et al.  Comparison of methods for determining coumarins in distilled beverages , 2000 .

[32]  H. Yamazaki,et al.  Highly sensitive high-performance liquid chromatographic assay for coumarin 7-hydroxylation and 7-ethoxycoumarin O-deethylation by human liver cytochrome P450 enzymes. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[33]  R. Bronaugh,et al.  Percutaneous Absorption and Metabolism of Coumarin in Human and Rat Skin , 1997, Journal of applied toxicology : JAT.

[34]  K. Ishimori,et al.  The distal glutamic acid as an acid-base catalyst in the distal site of horseradish peroxidase. , 1996, Biochemical and biophysical research communications.

[35]  C. Kappe.  100 years of the biginelli dihydropyrimidine synthesis , 1993 .

[36]  S. J. Bach,et al.  The catalytic effect of glutamic acid derivatives in urea synthesis. , 1960, Biochimica et biophysica acta.