Abstract
Efficient synthesis of 3,3′-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones) has been achieved by methanesulfonic acid-catalyzed, microwave-assisted reaction of 4-hydroxycoumarin and aromatic aldehydes in ethanol. The procedure has the advantages of high yield, short reaction time, low energy consumption, and convenient work-up. Compound structures were confirmed by IR, 1H NMR, and 13C NMR spectroscopy and by elemental analysis.
Similar content being viewed by others
References
J.H. Lee, H.B. Bang, S.Y. Han et al., Tetrahedron Lett. 48, 2889 (2007)
R.D.R.S. Manian, J. Jayashankaran, R. Raghunathan, Tetrahedron Lett. 48, 1385 (2007)
H. Zhao, N. Neamati, H. Hong et al., J. Med. Chem. 40, 242 (1997)
G.K. Maria, E.J. Marian, Med. Pharm. Chem. 3, 583 (1961)
I. Kostova, N. Trendafilova, G.J. Momekov, Inorg. Biochem. 99, 477 (2005)
M. Ilia, M.M. Caecilia, D. Nicolay, Eur. J. Med. Chem. 41, 882 (2006)
I.I. Manolov, Tetrahedron Lett. 39, 3041 (1998)
P.C.M. Mao, J.F. Mouscadet et al., Chem. Pharm. Bull. 50(12), 1634 (2002)
C.X. Su, J.F. Mouscadet, C.C. Chiang et al., Chem. Pharm. Bull. 54, 682 (2006)
J. Wang, D.Q. Shi, Q.Y. Zhuang et al., Chin. J. Org. Chem. 25, 926 (2005)
K. Mazaahir, V. Bansal, P. Mothsra et al., J. Mol. Catal. A: Chem. 268, 76 (2007)
A. Khodabocus, B.M.P. Beebeejaun, Sci. Technol. 5, 21 (2000)
M. Wang, Y. Liang, T. Zhang et al., Chin. J. Chem. 29, 1656 (2011)
V. Premasagar, V.A. Palaniswamy, E.J.J. Eisenbraun, Org. Chem. 46, 2974 (1981)
D. Kumar, S. Rudrawar, A.K. Chakraborti, Austr. J. of Chem. 61, 881 (2008)
Shen, Y. B. and Wang, G. W. ARKIVOC. (xvi), 1 (2008)
S.J. Tu, C.M. Li, G.G. Li et al., J. Comb. Chem. 9, 1144 (2007)
J.F. Zhou, G.X. Gong, K.B. Shi et al., Chin. Chem. Lett. 20, 672 (2009)
J.F. Zhou, G.X. Gong, H.Q. Zhu et al., Chin. Chem. Lett. 20, 1198 (2009)
J. Wang, S. Cheng, C.F. Gong et al., Chin. J. Chem. 29, 2101 (2011)
G.X. Gong, L.T. An et al., Chin. J. Org. Chem. 29, 1988 (2009)
Zhou, J. F.; Sun, X.J.; Lou, F. W. et al., Res Chem Intermed. 38, (2012). doi:10.1007/s11164-012-0696-5
M. Kidwai, V. Bansal, P. Mothsra et al., J. Mol. Catal. A: Chem. 268, 76 (2007)
J. Wang, D.Q. Shi, Q.Y. Zhuang et al., Chin. J. Org. Chem. 25, 926 (2005)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Qi, X., Xue, MW., Sun, XJ. et al. Microwave-assisted, methanesulfonic acid-catalyzed synthesis of 3,3′-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones). Res Chem Intermed 40, 1187–1192 (2014). https://doi.org/10.1007/s11164-013-1031-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-013-1031-5