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

Farhad  Hatamjafari ¹ (Department of Chemistry, Faculty of Science, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran)

Received: 2016-03-12 Accepted : 2018-10-29 Published : 2016-03-12

Keywords: One-pot, Biological activity, Multicomponent reaction, Glutamic acid, 4H-chromene,

Abstract :

In this study, the synthesis of 4H-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 1H 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.

References:

1. Kappe C.O., 1993. 100 years of the Biginelli dihydropyrimidine synthesis. Tetrahedron. 49(32), 6937ââ‚‌“6963.
2. Kappe C.O., 2000. Recent advances in the Biginelli dihydropyrimidine synthesis: new tricks from an old dog. Accounts Chem Res. 33(12), 879ââ‚‌“888.
3. 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.
4. 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, 1772ââ‚‌“1777.
5. 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), 1357ââ‚‌“1361.
6. 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.
7. Yourick J.J., Bronaugh R.L., 1997. Percutaneous Absorption and Metabolism of Coumarin in Human and Rat Skin. J Appl Toxicol. 17, 153ââ‚‌“158.
8. 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.
9. 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.
10. 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.
11. Guo S.B., Wang S.X., Li J.T., 2007. D, Lââ‚‌Prolineââ‚‌Catalyzed Oneââ‚‌Pot Synthesis of Pyrans and Pyrano [2,3ââ‚‌c] pyrazole Derivatives by a Grinding Method under Solventââ‚‌Free Conditions, Synth Commun. 37, 2111-2120.
12. 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.
13. 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.
14. Sabitha G., Arundhathi K., Sudhakar K., Sastry B.S., Yadav J.S., 2009. Cerium (III) Chlorideââ‚‌“Catalyzed One-Pot Synthesis of Tetrahydrobenzo [b] pyrans. Synth Commun. 39, 433-442.
15. 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.
16. 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.
17. 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.
18. Li J.T., Xu W.Z., Yang L.C., Li T.S., 2004. Oneââ‚‌Pot Synthesis of 2ââ‚‌Aminoââ‚‌4ââ‚‌arylââ‚‌3ââ‚‌carbalkoxyââ‚‌7,7ââ‚‌dimethylââ‚‌5,6,7,8ââ‚‌tetrahydrobenzo[b]pyran Derivatives Catalyzed by KF/Basic Al2O3 Under Ultrasound Irradiation. Synth Commun. 34, 4565-4571.
19. Hatamjafari F., 2014. Biological Activity and Efficient Synthesis of 3, 4-Dihydropyrimidin-2-(1H)-one/thione Derivatives. J Chem Health Risks. 4(4), 55ââ‚‌“61.
20. 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.
21. 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.
22. Hatamjafari F., 2006. New Protocol to Synthesize Spiroââ‚‌1,4ââ‚‌dihydropyridines by Using a Multicomponent Reaction of Cyclohexanone, Ethyl Cyanoacetate, Isatin, and Primary Amines under Microwave Irradiation. Synth Commun. 36, 3563-3570.
23. Grassl M., Bach S.J., 1960. The catalytic effect of glutamic acid derivatives in urea synthesis. Biochimica et Biophysica Acta. 42, 154-157.
24. 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.
25. Abbasi E., Hatamjafari F., 2013. Glutamic acid as an Efficient Catalyst for Synthesis of Dihydropyrimidinones. Oriental J Chem. 29, 731-733.
26. Hatamjafari F., Sabetpoor S., 2014. Synthesis of Coumarin Derivatives Using Glutamic Acid under Solvent-Free Conditions. Oriental J Chem. 30, 863-865.
27. Uma maheswari Devi P., Srinivasa Reddy P., Usha Rani N., R., Reddanna P., 2000. Lipoxygenase Metabolites of α-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.
28. 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.
29. 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.
30. 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.
31. 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.
32. 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.
33. 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.
34. 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.
35. 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.
36. Oskooie H.A., Heravi M.M., Karimi N., Ebrahimzadeh M., 2011. Caro's Acidââ‚‌“Silica Gel: An Efficient and Versatile Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives. Synth Commun. 41, 436-440.
37. 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.