Glutamic Acid as an Environmentally Friendly Catalyst for One-Pot Synthesis of 4H-Chromene Derivatives and Biological Activity
Subject Areas : Journal of Chemical Health Risks
1 - Department of Chemistry, Faculty of Science, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran
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Abstract :
- Kappe C.O., 1993. 100 years of the Biginelli dihydropyrimidine synthesis. Tetrahedron. 49(32), 6937âââ6963.
- Kappe C.O., 2000. Recent advances in the Biginelli dihydropyrimidine synthesis: new tricks from an old dog. Accounts Chem Res. 33(12), 879âââ888.
- Yue T., Wang M.X., Wang D.X., Masson G., Zhu J.P., 2009. Catalytic Asymmetric Passerini-Type Reaction: Chiral Aluminum-Organophosphate-Catalyzed Enantioselective alpha-Addition of Isocyanides to Aldehydes. J Organic Chem. 74 (21), 8396-8399.
- Trofimov B.A., Andriyankova L.V., Belyaeva K.V., 2010. C2-functionalization of 1-substituted imidazoles with aldehydes and electron-deficient acetylenes: a novel three-component reaction. Europ J Organic Chem. 9, 1772âââ1777.
- Ma N., Jiang B., Zhang G., Tu S.J., Wever W., Li G., 2010. 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. Green Chem. 12(8), 1357âââ1361.
- Hiroshi Y., Masaaki T., Tsutomu S., 1999. Highly sensitive high-performance liquid chromatographic assay for coumarin 7-hydroxylation and 7-ethoxycoumarin O-deethylation by human liver cytochrome P450 enzymes. J Chromato B: Biomed Sci Applications. 721(1), 13-19.
- Yourick J.J., Bronaugh R.L., 1997. Percutaneous Absorption and Metabolism of Coumarin in Human and Rat Skin. J Appl Toxicol. 17, 153âââ158.
- Izquierdo M.E.F., Granados J.Q., Mir V.M., Martinez M.C.L., 2000. Comparison of methods for determining coumarins in distilled beverages. Food Chem. 70, 251.
- Mohammad S., Hassan S., 2008. 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. Catalysis lett. 126, 275-279.
- Kumar D., Reddy V.B., Sharad S., Dube U., Kapur S., 2009. 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. Europ J Med Chem. 44, 3805-3809.
- Guo S.B., Wang S.X., Li J.T., 2007. D, LââÂProlineââÂCatalyzed OneââÂPot Synthesis of Pyrans and Pyrano [2,3ââÂc] pyrazole Derivatives by a Grinding Method under SolventââÂFree Conditions, Synth Commun. 37, 2111-2120.
- Balalaie S., Bararjanian M., Amani A.M., Movassagh B., 2006. (S)-Proline as a Neutral and Efficient Catalyst for the One-Pot Synthesis of Tetrahydrobenzo [b] pyran Derivatives in Aqueous Media. Synlett. 2, 263-266.
- Sun W.B., Zhang P., Fan J., Chen S.H., Zhang Z.H., 2010. Lithium Bromide as a Mild, Efficient, and Recyclable Catalyst for the One-Pot Synthesis of Tetrahydro-4H-Chromene Derivatives in Aqueous Media. Synth Commun. 40, 587-594.
- Sabitha G., Arundhathi K., Sudhakar K., Sastry B.S., Yadav J.S., 2009. Cerium (III) ChlorideâââCatalyzed One-Pot Synthesis of Tetrahydrobenzo [b] pyrans. Synth Commun. 39, 433-442.
- Pore D.M., Undale K.A., Dongare B.B., Desai U.V., 2009. Potassium Phosphate Catalyzed a Rapid Three-Component Synthesis of Tetrahydrobenzo [b] pyran at Ambient Temperature. Catalysis lett. 132, 104-108.
- El-Rahaman N.M.A., El-Kateb A.A., Mady M.F., 2007. Simplified Approach to the Uncatalyzed Knoevenagel Condensation and Michael Addition Reactions in Water using Microwave Irradiation. Synth Commun. 37, 3961-3970.
- Tu S.J., Gao Y., Guo C., Shi D., Lu Z., 2002. 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. Synth Commun. 32, 2137-2141.
- Li J.T., Xu W.Z., Yang L.C., Li T.S., 2004. OneââÂPot Synthesis of 2ââÂAminoââÂ4ââÂarylââÂ3ââÂcarbalkoxyââÂ7,7ââÂdimethylââÂ5,6,7,8ââÂtetrahydrobenzo[b]pyran Derivatives Catalyzed by KF/Basic Al2O3 Under Ultrasound Irradiation. Synth Commun. 34, 4565-4571.
- Hatamjafari F., 2014. Biological Activity and Efficient Synthesis of 3, 4-Dihydropyrimidin-2-(1H)-one/thione Derivatives. J Chem Health Risks. 4(4), 55âââ61.
- Azizian J., Hatamjafari F., Karimi A.R., Shaabanzadeh M., 2006. Multi-Component Reaction of Amines, Alkyl Propiolates, and Ninhydrin: An Efficient Protocol for the Synthesis of Tetrahydro-dihydroxy-oxoindeno [1,2-b] pyrrole Derivatives. Synthesis. 5, 765-767.
- Azizian J., Shaabanzadeh M., Hatamjafari F., Mohammadizadeh M.R., 2006. 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. Arkivoc. xi, 47-58.
- Hatamjafari F., 2006. New Protocol to Synthesize SpiroââÂ1,4ââÂdihydropyridines by Using a Multicomponent Reaction of Cyclohexanone, Ethyl Cyanoacetate, Isatin, and Primary Amines under Microwave Irradiation. Synth Commun. 36, 3563-3570.
- Grassl M., Bach S.J., 1960. The catalytic effect of glutamic acid derivatives in urea synthesis. Biochimica et Biophysica Acta. 42, 154-157.
- Tanaka M., Ishimori K., Morishima I., 1996. The Distal Glutamic Acid as an Acid-Base Catalyst in the Distal Site of Horseradish Peroxidase. Biochem Biophy Res Commun. 227, 393-399.
- Abbasi E., Hatamjafari F., 2013. Glutamic acid as an Efficient Catalyst for Synthesis of Dihydropyrimidinones. Oriental J Chem. 29, 731-733.
- Hatamjafari F., Sabetpoor S., 2014. Synthesis of Coumarin Derivatives Using Glutamic Acid under Solvent-Free Conditions. Oriental J Chem. 30, 863-865.
- Uma maheswari Devi P., Srinivasa Reddy P., Usha Rani N., R., Reddanna P., 2000. Lipoxygenase Metabolites of ñ-linolenic Acid in the Development of Resistance in Pigeonpea, Cajanus cajan (L.) Millsp, Seedlings Against Fusarium udum Infection. Europ J Plant Pathol. 106(9), 857-865.
- Colle J.G., Duguid J.P., Firaser A.G., Mannion B.P., 1989. Mackie & Mecartney Practical Medicinal Microbiology. Thirteenth Edition. Churchil, Edinburgh and London. 2, 553-558.
- Sarrafi Y., Mehrasbi E., Vahid A., Tajbakhsh M., 2012. Well-Ordered Mesoporous Silica Nanoparticles as a Recoverable Catalyst for One-Pot Multicomponent Synthesis of 4H-Chromene Derivatives. Chinese J Catalysis. 33, 1486-1494.
- Dekamin M.G., Eslami M., Maleki A., 2013. 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. Tetrahedron. 69, 1074-1085.
- Zheng J., Li Y.Q., 2011. One-pot synthesis of tetrahydrobenzo [b] pyran and dihydropyrano [c] chromene derivatives in aqueous media by using trisodium citrate as a green catalyst. Arch Appl Sci Res. 3(2), 381-388.
- Dzierzak J., Lefenfeld M., Raja R., 2009. Single-site Biomimetic Amino Acid Complexes for the Benign Oxidation of Hydrocarbons and Alcohols. Topics in Catalysis. 52, 1669-1676.
- Devi I., Bhuyan P.J., 2004. Sodium bromide cata-lysed one-pot synthesis of tetrahydrobenzo [b] pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions. Tetrahedron Lett. 45, 8625-8627.
- Davoodnia A., Allameh S., Fazli S., Tavakoli-Hoseini N., 2011. 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. Chem papers. 65, 714-720.
- Hekmatshoar R., Majedi S., Bakhtiari. K., 2008. Sodium selenate catalyzed simple and efficient synthesis of tetrahydro benzo [b] pyran derivatives. Catalysis Commun. 9, 307-310.
- Oskooie H.A., Heravi M.M., Karimi N., Ebrahimzadeh M., 2011. Caro's AcidâââSilica Gel: An Efficient and Versatile Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives. Synth Commun. 41, 436-440.
- Vahdat S.M., Khavarpour M., Mohanazadeh F., 2015. A Facile and Highly Efficient Three Component Synthesis of Pyran and Chromene Derivatives in the Presence of Nano SnO2 as a catalyst. J Appl Chem. 9, 41-46.