Abstract
A simple and concise method catalyzed by nanocrystalline ZnZr4(PO4)6 ceramics has been reported for the synthesis of a series of trans-2-benzoyl-3-(aryl)-2H-furo[3,2-c]chromen-4(3H)-ones using a multicomponent reaction of 2,4′-dibromoacetophenone, benzaldehydes and 4-hydroxycoumarin under microwave irradiation. This method provides several advantages including easy workup, excellent yields, short reaction times, using of microwave as clean method, recoverability of the catalyst and little catalyst loading.
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S. Sardari, Y. Mori, K. Horita, R.G. Micetich, S. Nishibe, M. Daneshtalab, Bioorg. Med. Chem. 7, 1933 (1999)
A.G. Al-Sehemi, S.R. El-Gogary, Chin. J. Chem. 30, 316 (2012)
M. Campos-Toimil, F. Orallo, L. Santana, E. Uriarte, Bioorg. Med. Chem. Lett. 12, 783 (2002)
L. Piccagli, M. Borgatti, E. Nicolis, N. Bianchi, I. Mancini, I. Lampronti, D. Vevaldi, F.D. Acqua, G. Cabrini, R. Gambari, Bioorg. Med. Chem. 18, 8341 (2010)
M. Borgatti, A. Chilin, L. Piccagli, I. Lampronti, N. Bianchi, I. Mancini, G. Marzaro, F. dall’Acqua, A. Guiotto, R. Gambari, Eur. J. Med. Chem. 46, 4870 (2011)
T.O. Olomola, S. Mosebi, R. Klein, T. Traut-Johnstone, J. Coates, R. Hewer, P.T. Kaye, Bioorg. Chem. 57, 1 (2014)
J. Safaei-Ghomi, B. Khojastehbakht-Koopaei, H. Shahbazi-Alavi, RSC Adv. 4, 46106 (2014)
Y. Gu, Green Chem. 14, 2091 (2012)
E. Altieri, M. Cordaro, G. Grassi, F. Risitano, A. Scala, Tetrahedron 66, 9493 (2010)
S. Michael Rajesh, S. Perumal, J.C. Menendez, S. Pandian, R. Murugesan, Tetrahedron 68, 5631 (2010)
X.C. Tan, H.Y. Zhao, Y.M. Pan, N. Wu, H.S. Wang, Z.F. Chen, RSC Adv. 5, 4972 (2015)
W.L. Zhang, S.N. Yue, Y.M. Shen, H.Y. Hu, Q.-H. Meng, H. Wu, Y. Liu, Org. Biomol. Chem. 13, 3602 (2015)
A. Kumar, S. Srivastava, G. Gupta, Green Chem. 14, 3269 (2012)
Q.F. Wang, H. Hou, L. Hui, C.G. Yan, J. Org. Chem. 74, 7403 (2009)
C.J. Lee, C.C. Tsai, S.H. Hong, G.H. Chang, M.C. Yang, L. Mohlmann, W. Lin, Angew. Chem. 54, 8502 (2015)
S.R. Elgogary, N.M. Hashem, M.N. Khodeir, J. Heterocycl. Chem. 52, 506 (2015)
G. Karthik, T. Rajasekaran, B. Sridhar, B.V. Subba Reddy, Tetrahedron 70, 8148 (2014)
A. Dongamanti, V.L. Bommidi, G. Arram, R. Sidda, Heterocycl. Commun. 20, 293 (2014)
S.L. Wang, F.Y. Wu, C. Cheng, G. Zhang, Y.P. Liu, B. Jiang, F. Shi, S.J. Tu, ACS Comb. Sci. 13, 135 (2011)
A. Bruckmann, A. Krebs, C. Bolm, Green Chem. 10, 1131 (2008)
S. Santra, P.R. Andreana, Org. Lett. 9, 5035 (2007)
S.L. Cui, X.F. Lin, Y.G. Wang, J. Org. Chem. 70, 2866 (2005)
J. Safaei-Ghomi, E. Heidari-Baghbahadorani, H. Shahbazi-Alavi, M. Asgari-Kheirabadi, RSC Adv. 5, 18145 (2015)
V. Polshettiwar, R.S. Varma, Green Chem. 12, 743 (2010)
N. Gorodylova, V. Kosinova, Z. Dohnalova, P. Belina, P. Sulcova, Dyes Pigm. 98, 393 (2013)
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The authors acknowledge a reviewer who provided helpful insights. The authors gratefully acknowledge the financial support of this work by the Research Affairs Office of the Islamic Azad University, Qom Branch, Qom, I. R. Iran.
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Safaei-Ghomi, J., Babaei, P., Shahbazi-Alavi, H. et al. A concise synthesis of furo[3,2-c]coumarins catalyzed by nanocrystalline ZnZr4(PO4)6 ceramics under microwave irradiation. J IRAN CHEM SOC 13, 1439–1448 (2016). https://doi.org/10.1007/s13738-016-0859-1
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DOI: https://doi.org/10.1007/s13738-016-0859-1