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A Facile, Eco-friendly, Proton Donor-Acceptor Catalyzed, One-Pot, Three-Component Synthesis of Tetrahydrobenzo[b]pyrans
Corresponding Author(s) : A. Indrasena
Asian Journal of Chemistry,
Vol. 26 No. 8 (2014): Vol 26 Issue 8
Abstract
Piperidinium acetate catalyzed, three-component cyclocondensation between aryl aldehydes (1), malononitrile (2) and cyclic-1,3-diketo compounds (3) in the eco-friendly and universal solvent water at room temperature for 0.5 h, resulted in the formation of tetrahydro[b]pyran derivatives (4). The formation of 4 could also be established in a step-wise fashion by isolating independently each of the intermediates benzylidine malononitrile 5 and benzylidine cyclohexane-1,3-dione 6 and treating them subsequently with 3 and 2, respectively to obtain benzopyrans 4. Mechanistic studies on the formation of 4 from 1, 2 and 3 are reported. Further, the synthesis of 4 could also be achieved in two variable but identical end-product giving tandem syntheses by treating 1 with 2 and then with 3 giving 4 or by treating 1 with 3 and then with 2 giving 4. All the products were suitably characterized using NMR, IR and Mass spectroscopy.
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References
(a) D. Dallinger, N.Y. Gorobets and C.O. Kappe, Org. Lett., 5, 1205 (2003); doi:10.1021/ol034085v.; (b) A.M. Shestopalov, Y.M. Emeliyanova, A.A. Shestopalov, L.A. Rodinovskaya, Z.I. Niazimbetova and D.H. Evans, Org. Lett., 4, 423 (2002); doi:10.1021/ol0102747.; (c) B. List and C. Castello, Synlett, 1687 (2001); doi:10.1055/s-2001-18095.; (d) H.Z. Syeda Huma, R. Halder, S.S. Kalra, J. Das and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); doi:10.1016/S0040-4039(02)01240-6; (e) F. Bertozzi, M. Gustafsson and R. Olsson, Org. Lett., 4, 3147 (2002); doi:10.1021/ol0264814.; (f) U. Bora, A. Saikia and R.C. Boruah, Org. Lett., 5, 435 (2003); doi:10.1021/ol020238n.; (g) V. Nair, A.U. Vinod and C. Rajesh, J. Org. Chem., 66, 4427 (2001); doi:10.1021/jo001714v.; (h) J.-F. Cheng, M. Chen, T. Arrhenius and A. Nadzan, Tetrahedron Lett., 43, 6293 (2002); doi:10.1016/S0040-4039(02)01403-X.; (i) M.C. Bagley, J.W. Dale and J. Bower, Chem. Commun., 1682 (2002); doi:10.1039/b203900a.; (j) Y. Yuan, X. Li and K. Ding, Org. Lett., 4, 3309 (2002); doi:10.1021/ol0265822.
(a) E.C. Witte, P. Neubert and A. Roesch, Chem. Abstr., 104, 224915f (1986); (b) L. Bonsignore, G. Loy, D. Secci and A. Calignano, Eur. J. Med. Chem., 28, 517 (1993); doi:10.1016/0223-5234(93)90020-F.; (c) L. Andreani and E. Lapi, Bull. Chim. Farm, 99, 583 (1960).
K. Singh, J. Singh and H. Singh, Tetrahedron, 52, 14273 (1996); doi:10.1016/0040-4020(96)00879-4.
G. Kaupp, M.R. Naimi-Zamal and J. Schmeyers, Tetrahedron, 59, 3753 (2003); doi:10.1016/S0040-4020(03)00554-4.
A. Mobinikhaledi and A.B. Mohammad, Acta Chim. Slov., 57, 931 (2010) and references cited therein.
S. Mahalle, D. Ligampalle and R. Mane, Heteroatom Chem., 20, 151 (2009); doi:10.1002/hc.20528.
R. Nikitas, Tetrahedron Lett., 28, 93 (1987); doi:10.1016/S0040-4039(00)95658-2.
R.B. Lesyk and B.S. Zimenkovsky, Curr. Org. Chem., 8, 1547 (2004); doi:10.2174/1385272043369773.
S. Ravi, K.K. Chiruvella, K. Rajesh, V. Prabhu and S.C. Raghavan, Eur. J. Med. Chem., 45, 2748 (2010); doi:10.1016/j.ejmech.2010.02.054.
T.-P. Loh, L.-C. Feng, H.-Y. Yang and J.-Y. Yang, Tetrahedron Lett., 43, 8741 (2002); doi:10.1016/S0040-4039(02)02104-4.
Sd. Riyazd, A. Naidu and P.K. Dubey, Indian J. Chem., 51B, 1396 (2012).
P.K. Dubey and M. Venkatanarayana, Green Chem. Lett. Rev., 3, 257 (2010); doi:10.1080/17518251003749379.