Silica gel: A very cheap, reusable, and efficient catalyst for green preparation of some bis-4-hydroxycoumarin on water

Authors

Young Researchers and Elite Club, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.

Abstract

Silica gel has been used for synthesis of biscoumarin derivatives starting from 4-hydroxycoumarin and aryl aldehydes. The reaction conditions are completely in agreement with green chemistry principles including sing water as media and a recyclable and safe catalyst. This method is also simple and inexpensive and leads to high yield of products in short reaction times.

Keywords


[1] B. Karami, S. Khodabakhshi, K. Eskandari, Tetrahedron Lett. 53 (2012) 1445-1446.
[2] (a) G. Appendino, G. Cravotto, S. Tagliapietra, S. Ferraro, G.M. Nano, G. Palmisano, Helv. Chim. Acta 74 (1991) 1451-1458. (b) I. Manolov, C.M. Moessmer, N.D. Danchev, Eur. J. Med. Chem. 41 (2006) 882-890.
[3] R.D.H. Murray, J. Mendez, S.A. Brown, The Natural Coumarins: Occurrence, Chemistry and Biochemistry; Wiley & Sons: Chichester, 1982.
[4] R.S. Overmann, M.A. Stahmann, C.F. Heubner, W.R. Sullivan, L. Spero, D.G. Doherty, M. Ikawa, L. Graf, S. Roseman, K.P. Link, J. Biol. Chem. 153 (1944) 5-24.
[5] J. Lehmann, The Lancet 241 (1943) 611-613.
[6] V. Padalkar, K. Phatangare, S. Takale, R. Pisal, A. Chaskar, J. Saudi Chem. Soc. (2012) In Press.
[7] I. Manolov, C. Maichle-Moessmer, N. Danchev, Eur. J. Med. Chem. 41 (2006) 882-890.
[8] M.M. Heravi, F. Nahavandi, S. Sadjadi, H.A. Oskooie, F.F. Bamoharram, Synth. Commun. 40 (2010) 498-503.
[9] (a) W. Li, Y. Wang, Z. Wang, L. Dai, Y. Wang, Catal. Lett. 141 (2011) 1651-1658. (b) B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53 (2012) 4343-4346. (c) A.M.A. Al-Kadasi, G.M. Nazeruddin, Int. J. Chem. Sci. 10 (2012) 324-330. (d) Z. Karimi-Jaberi, M.R. Nazarifar, B. Pooladian, Chin. Chem. Lett. 23 (2012) 781-784.
[10] M.M. Heravi, S. Sadjadi, N. Mokhtari Haj, H.A. Oskooie, F.F. Bamoharram, Catal. Commun. 10 (2009) 1643-1646.
[11] G.-X. Gong, J.-F. Zhou, L.-T. An, X.-L. Duan, S.-J. Ji, Synth. Commun. 39 (2009) 497-505.
[12] M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 268 (2007) 76-81.
 
[13] R.S. Joshi, P.G. Mandhane, S.K. Dabhade, C.H. Gill, J. Chin. Chem. Soc. 58 (2010) 1227-1231.
[14] A. Chanda, V.V. Fokin, Chem. Rev. 109 (2009) 725-748.
[15] F. Jafari, S. Khodabakhshi, Der Chemica Sinica 3 (2012) 775-779.
[16] S. Khodabakhshi, B. Karami, Catal. Sci. Technol. 2 (2012) 1940-1944.
[17] B. Karami, V. Ghashghaee, S. Khodabakhshi, Catal. Commun. 20 (2012) 71-75.
[18] B. Karami, S. Khodabakhshi, M. Nikrooz, Polycyclic Aromat. Compd. 31 (2011) 97-109.
[19] D. Zavrsnik, S. Muratovic, D. Makuc, J. Plavec, M. Cetina, A. Nagl, E.D. Clercq, J. Balzarini, M. Mintas, Molecules 16 (2011) 6023-6040.
[20] P. Singh, P. Kumar, A. Katyal, R. Kalra, S.K. Dass, S. Prakash, R. Chandra, Catal. Lett. 134 (2010) 303-308.
[21] A.M. A. Al-Kadasi, G.M. Nazeruddin, Int. J. Chem. Sci. 10 (2012) 324-330.
[22] A.D. Gupta, S. Samanta, R. Mondal, A.K. Mallik, Bull. Korean Chem. Soc. 33 (2012) 4239-4242.