Eggshell: A green and efficient heterogeneous catalyst for the synthesis of pyrano[3,2-c]quinoline
محورهای موضوعی : Iranian Journal of CatalysisLeila Youseftabar-Miri 1 , Fatemeh Akbari 2 , Farshid Ghraghsahar 3
1 - Department of Chemistry, Izeh Branch, Islamic Azad University, Izeh, Iran.
2 - Department of Chemistry, Science and Research Branch, Islamic Azad University, Ahwaz, Iran.
3 - Department of Chemistry, Science and Research Branch, Islamic Azad University, Ahwaz, Iran.
کلید واژه: Heterogeneous catalyst, Multicomponent reactions, Pyranoquinoline, Eggshell,
چکیده مقاله :
Eggshell was found to be a versatile heterogeneous catalyst for the synthesis of pyrano[3,2-c]quinoline derivatives in good yields. This protocol has the advantages of environmental friendliness, short reaction time, low cost and convenient operation.
[1] N. Mont, J. Teixido׳, J.I. Borrell, C.O. Kappe, Tetrahedron Lett. 44 (2003) 5385-5387. (b) M.C. Bagley, J.W. Dale, J. Bower, Chem. Commun. (2002) 1682-1683. (c) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 24 (2004) 4957-4980. (d) Y.J. Huang, F.Y. Yang, C.J. Zhu. J. Am. Chem. Soc. 127 (2005) 16386-16387.
[2] M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108 (2008) 2015-2050.
[3] (a) J. Zhu, H. Bienayme, H. Multicomponent Reactions; Wiley: New York, (2005). (b) S.L. Cui, X.F. Lin, Y.G. Wang. J. Org. Chem. 70 (2005) 2866-2869.
[4] (a) C.J, Li, T.H Chan. Organic Reactions in Aqueous Media; Wiley: New York, (1997). (b) P.A. Grieco. Ed.; Thomson Science: Glasgow, Scotland, Organic Synthesis in Water. (1998). (c) C.J. Li. Chem. Rev.105 (2005) 3095-3166.
[5] S.K. Kulkarni, P.N. Kaul. Indian J. Exp. Biol. 18 (1980) 270-272.
[6] (a) H. Tomoda, Y.K. Kim, H. Nishida, R. Masuma, S. Omura, J. Antibiot. 47 (1994) 148-153. (b) M. Handa, T. Sunazuka, K. Nagai, R. Kimura, T. Shirahata, Z.M. Tian, K. Otoguro, Y. Harigaya, S. Omura, J. Antibiot. 54 (2001) 382-389.
[7] T.S., Chen, S.J. Wu, I.L. Tsai, T.S., Wu, J.M. Pezzuto, M.C. Lu, H. Chai, N. Suh, C.M. Teng, J. Nat. Prod. 57 (1994) 1206-1211.
[8] (a) T. Davion, B. Joseph, Y. Merour. Synlett (1998) 1051-1052. (b) L. F. Tietze, Y. F. Zhou. Angew. Chem. Int. Ed. 38 (1999) 2045-2047. (c) Y. Fujita, H. Oguri, H. Oikawa. J. Antibiot. 58 (2005) 425-427.
[9] F. Hanawa, N. Fokialakis, A.L. Skaltsounis, Planta Med. 70 (2004) 531-535.
[10] C.L. Cantrell, K.K. Schrader, L.K. Mamonov, G.T. Sitpaeva, T. S. Kustova, C. Dunbar, D.E. Wedge. J. Agric. Food Chem. 53 (2005) 7741-7748.
[11] J.J. Chen, P.H. Liao, C. H. Huang, S. Y. Chen. J. Nat. Prod. 70 (2007) 1444-1448.
[12] F. Koizumi, N. Fukumitsu, J. Zhao, R. Chanklan, T. Miyakawa, S. Kawahara, S. Iwamoto, M. Suzuki, S. Kakita, E.S. Rahayu, S. Hosokawa, K. Tatsuta, M. Ichimura. J. Antibiot. 60 (2007) 455-458.
[13] I.S. Chen, I.W. Tsai, C.M. Teng, J.J. Chen, Y.L. Chang, F.N. Ko, M.C. Lu. Phytochemistry 46 (1997) 525-529.
[14] C. Ito, M. Itoigawa, A. Furukawa, T. Hirano, T. Murata, N. Kaneda, Y. Hisada, K. Okuda, H. Furukawa. J. Nat. Prod. 67 (2004) 1800-1803.
[15] I.S. Chen, S.J. Wu, I.L. Tsai, T.S. Wu, J.M. Pezzuto, M.C. Lu, H. Chai, N. Suh, C.M. Teng. J. Nat. Prod. 57 (1994) 1206-1211.
[16] X. Wang, Z. Zeng, D. Shi, X. Wei, Z. Zong, Synth. Commun. 34 (2004) 3021-3027.
[17] M. Lei, L. Mab, L. Hu, Tetrahedron Lett. 52 (2011) 2597-2600.
[18] (a) I.V. Magedov, M. Manpadi, E. Rozhkova, N.M. Przheval’skii, S. Rogelj, S.T. Shors, W.F.A. Steelant, S. Van Slambrouck, A. Kornienko, Bioorg. Med. Chem. Lett. 17 (2007) 1381-1385. (b) I.V. Magedov, M. Manpadi, M.A. Ogasawara, A.S. Dhawan, S. Rogelj, S. Van slambrouck, W.F.A. Steelant, N.M. Evdokimov, P.Y. Uglinskii, E.M. Elias, E.J. Knee, P. Tongwa, M. Yu. Antipin, A. Kornienko, J. Med. Chem. 51 (2008) 2561-2570. (c) X. Fan, D. Feng, Y. Qu, X. Zhang, J. Wang, P.M. Loiseau, G. Andrei, R. Snoeck, E. Clercq, Bioorg. Med. Chem. Lett. 20 (2010) 809-813.
[19] (a) G. Rossini, R. Ballini, P. Sorrenti, Synthesis (1983) 1014-1016. (b) R. Ballini, G. Bosica, J. Org. Chem. 62 (1997) 425-427.
[20] E. Mosaddegh, A. Hassankhani, Catal. Commun. 33 (2013) 70-75.
[21] Y.C. Sharma, B. Singh, J. Korstad, Energy Fuels 24 (2010) 3223–3231.
[22] G. Krithiga, T.P. Sastry, Bull. Mater. Sci. 34 (2011) 177–181.
[23] W.N. Garnjanagoonchorn, A. Changpuak, Int. J. Food Prop. 10 (2007) 497–503.
[24] H.J. Park, S.W. Jeong, J.K. Yang, B.G. Kim, S.M. Lee, J. Environ. Sci. 19 (2007) 1436-1441.
[25] K. Rad-Moghadam, S.C. Azimi, E. Abbaspour-Gilandeh, Tetrahedron Lett. 54 (2013) 4633-4645.
[26] K. Rad-Moghadam, L. Youseftabar-Miri. J. Fluorine Chem. 135 (2012) 213-219.
[27] K. Rad-Moghadam, L. Youseftabar-Miri. Tetrahedron 67 (2011) 5693-5699.
