Highly efficient synthesis of tetrahydrobenzo[b]pyrans under visible light promoted by cesium carbonate

Kamble, Vinod; Sadaf, Munazza; Saleh, Bushra

Document Type : Short communication

Authors

¹ Organic Chemistry Research Laboratory, Department of Chemistry, Institute of Science, Nagpur-440001, India

² Organic Chemistry Research Laboratory, School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Vishnupuri, Nanded- 431606, India

Abstract

Multi-component coupling reaction (MCR) is a powerful synthetic tool for the synthesis of biologically active compounds. Development of such multi-component coupling reaction strategies in visible light has been of considerable interest, as they provide simple and rapid access to a large number of organic molecules through a sustainable path. An efficient and green protocol for the synthesis of tetrahydrobenzo[b]pyrans derivatives by one-pot, three component coupling reaction of aromatic aldehyde, malononitrile, and dimedone has been developed using readily available cesium carbonate as the catalyst under visible light. This efficient procedure has the advantages of giving the target compounds in high yields, short reaction times, simple work-up procedure, use of chief and easily available catalyst, and environmentally benign conditions.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] G.R. Green, J.M. Evans, A.K. Vong, in: A.R. Ktritsky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry II,5, Permagon Press, Oxford, 1995, p. 469.

[2] L. Bonsignore, G. Loy, D. Secci, A. Calignano, European Journal of Medicinal Chemistry, 1993, 28, 517-520..

[3] W.O. Foye, Principi di ChimicaFarmaceutica, II, Piccin, ed, Padua., 1991, 416-420.

[4] L.L. Andreani, E. Lepi, Bull. Chim.Farm., 1960, 99, 583-586.

[5] C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F.W. Keana, Chem. Abstr., 2000, 134, 29313a.

[6] C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F.W. Keana, PCT Int. Appl., 2000, WO 00, 75, 123.

[7] S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc. Chem. Commun., 1988, 17, 1202-1204.

[8] X.S. Wang, S.T. Tu, C.S. Yao, Synth. Commun., 2003, 33, 119-126.

[9] D. Arnesto, W.M. Horspool, N. Martin, A. Ramos, C. Seaone, J. Org. Chem., 1989, 54, 3069-3072.

[10] S. Tu, H. Jian, Q. Zhuang, C. Miao,D. Shi, X. Wang, G. Yuan, J. Org. Chem., 2003, 23, 488-490.

[11] J. Zhou, S. Tu, Y. Gao, M. Ji, Chin. J. Org. Chem., 2001, 21, 742-745.

[12] A. Masoumnia, S. Kiaee, J. Aboonajmi, N. Hazeri, Research in Pharmaceutical Sciences., 2012, 7 (1), S508.

[13] J. Albadi, M. Fadaeian, AbariF.Iran JOC, 2013, 5, 1089-1092.

[14] D. Shi, J. Mou, Q. Zhuang, X. Wang, J.of Chem. Res., 2004, 12, 821-823.

[15] N. Hazeri, M. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashi, Chin. J. of Catal., 2014, 35, 391-395.

[16] S. Rathod, B. Arbad, M. Lande, Chin. J.of Catal., 2010, 31, 631-636.

[17] J. Safaei, R. Teymuri, H. Shahbazi, A. Ziarati, Chem. Lett., 2013, 24, 921-925.

[18] L. Fotouhi, M.M Heravi, A. Fatehi, K. Bakhtiari, Tetrahedron Lett., 2011, 48,5379-5381.

[19] S. Daqing, Z. Shu, Q. Zhuang, T. Shujiang, H. Hongwen, Chin. J. Org. Chem., 2003, 23, 877-879.

[20] S. Balalaie, M. Bararjanian, A.M. Amani, B. Movassagh, Synlett, 2006, 2, 263-266.

[21] U.R. Pratap, D.V. Jawale, P.D. Netankar, R.A. Mane, Tetrahedron Lett., 2011, 52, 5817-5819.

[22] Y. Zhenjun, X. Renbo, S. Xusheng, L. Zhong, Tetrahedron Lett., 2010, 51, 4991-4995.

[23] N. Sara, B. Raouf,C. Bertrand, D. Abdelmadjid, C.R.Chimie, 2012, 15, 394-397.

[24] Y. Ren Y, C. Cai, Catal. Commun., 2008, 9, 1017-1020.

[25] S. Balalaie, M. Ahmadi, M. Barazjanian,Catal. Commun., 2007, 8, 1724-1727.

[26] W. Sun, P. Zhang,J. Fan, S. Chen, Z. Zhang, Synth. Commun., 2010, 40, 587-594.

[27] M. Khoobi, L.Mamani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. of Mol.Catal. A: Chem., 2012, 359, 74-80.

[28] S. Gurumurthi, V. Sundari, R. Valliappan, E-Journal of Chem., 2009, 6, 466-472.

[29] B. Boumoud, A.A. Yahiaoui, T. Boumoud, A. Debache, J. of Chem. & Pharm. Res., 2012, 4, 795-799.

[30] K. Samad, R. Ahmed, T. Saeed, J. of Fluorine Chem., 2012, 141, 83-89.

[31] B. Reddy, M. Patil, K. Rao, G. Reddy, J. Mol. Catal. A: Chem., 2006, 258, 302-307.

[32] N. Hoffmann, Chem. Rev., 2008, 108, 1052–1103.

[33] M. Fagnoni, D. Dondi, D. Ravelli, A. Albini, Chem. Rev., 2007, 107, 2725–2756.

[34] (a) J.P. Parrish, E.E. Dueno, S. Kim, K.W. Jung, Synth. Commun., 2000, 30(15), 2687-2690. (b) E.E. Dueno, F. Chu, S. Kim, K.W. Jung, Tetrahedron Lett., 1999, 40, 1843-1846.

[35] J. Butler, R.M. Kellogg, J. Org. Chem., 1981, 46, 4481-4485.

[36] F. Vogtle, W. Kissener, Chem. Ber.-Recueil., 1984, 117, 2538-2541.

[37] G. Dijkstra, W.H. Kruizinga, R.M. Kellogg, J. Org. Chem., 1987, 52, 4230-4234.

[38] Z. Blum, ActaChemicaScandinavica., 1989, 43, 248-250

[39] A. Ostrowicki, E. Koepp, F. Vogtle, TopicsInCurr. Chem., 1992, 161, 37-67.

[40] T. Flessner, S. Doye, J. Prak. Chem., 1999, 341, 186-190.

[41] R.N. Salvatore, A.S. Nagle, K.W. Jung, J.Org. Chem., 2002, 67, 674-683.

Iranian chemical communication

Highly efficient synthesis of tetrahydrobenzo[b]pyrans under visible light promoted by cesium carbonate

References

References

Volume 5, Issue 2, pp. 121-236, Serial No. 15
April 2017
Pages 167-172

Highly efficient synthesis of tetrahydrobenzo[b]pyrans under visible light promoted by cesium carbonate

References

References

Volume 5, Issue 2, pp. 121-236, Serial No. 15April 2017Pages 167-172

Volume 5, Issue 2, pp. 121-236, Serial No. 15
April 2017
Pages 167-172