Et3N as a catalyst for the synthesis of indeno[1,2-b]chromene derivatives via three-component condensation reaction

Iranian Journal of Catalysis

مقاله 8، دوره 5، شماره 4، اسفند 2015، صفحه 345-350   

نوع مقاله: Articles

نویسندگان

Ali Sadeghi^{* 1}؛ Ali Hossein Rezayan²؛ Ali Farajtabar¹

¹Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran.

²Department of Life Science Engineering, Faculty of New Sciences and Technologies, University of Tehran, Tehran, Iran.

چکیده

Functionalized indeno[1,2-b]chromene derivatives have been synthesized via condensation reaction of 1H-indene-1,3(2H)-dione with benzaldehyde and cyclization with 2-hydroxynaphthalene-1,4-dione in the presence of a catalytic amount of triethylamine (Et3N) in EtOH at room temperature. It was observed that benzaldehyde bearing electron donating group gave high yield of product, whereas, benzaldehyde having electronic withdrawing substituent does not participate in this reaction. The structures were confirmed spectroscopically (IR, 1H- and 13C-NMR, and Mass). A plausible mechanism for this reaction is proposed (Scheme 2). Good yields and easy purification are the main advantages of the present method. Products of these reactions have structural similarity to naturally occurring pyranokunthone B, lambertellin, β-lapachone, and α-xiloidone.

کلیدواژه‌ها

Indeno[1,2-b]chromene؛ Condensation reaction؛ 1H-Indene-1,3(2H)-dione؛ 2-Hydroxynaphthalene-1,4-dione

مراجع

[1] C.J. Li, Y.L. Li, U.S. Patent Appl. Publ. US (2005) 2005222246 A1 20051006.
[2] M. Ough, A. Lewis, E.A. Bey, J. Gao, J.M. Ritchie, W. Bornmann, D.A. Boothman, L.W. Oberley, J.J. Cullen, Canc. Biol. Ther. 4 (2005) 95-102.
[3] D.O. Moon, Y.H. Choi, N.D. Kim, Y.M. Park, G.Y. Kim, Int. Immunopharmacol. 7 (2007) 506-514.
[4] V.F. De Andrade-Neto, M.O.F. Goulart, J.F. Da Silva Filho, M.J. Da Silva, M.D.C.F. R. Pinto, A.V. Pinto, M.G. Zalis, L.H. Carvalho, A.U. Krettli, Bioorg. Med. Chem. Lett. 14 (2004) 1145-1149.
[5] P.S. Elisa, E. B. Ana, A.G. Ravelo, D.J. Yapu, A.G. Turba, Chem. Biodiversity 2 (2005) 264-274.
[6] A.M. Shestopalov, Y.M. Emelianova, V.N. Nesterov, Russ. Chem. Bull. 52 (2003) 1164-1171.
[7] A.J.M. da Silva, C.D. Buarque, F.V. Brito, L. Aurelian, L.F. Macedo, L.H. Malkas, R.J. Hickey, D.V.S. Lopes, F. Noël, Y.L.B. Murakami, N.M.V. Silva, P.A. Melo, R.R.B. Caruso, N.G. Castro, P.R.R. Costa, Bioorg. Med. Chem. 10 (2002) 2731-2738.
[8] G. Qabaja, G.B. Jones, J. Org. Chem. 65 (2000) 7187-7194.
[9] M. Rueping, E. Sugiono, E. Merino, Angew. Chem. Inter. Ed. 47 (2008) 3046-3049.
[10] P.M. Brown, V. Krishnamoorthy, J.W. Mathieson, R.H. Thomson, J. Chem. Soc. C (1970) 109-110.
[11] G.W. Kabalka, B. Venkataiah, D.C. Bhaskar, Synlett (2004) 2194.
[12] K.Tabatabaeian, H. Heidari, M.Mamaghani, N.O. Mahmoodi, Appl. Organometal. Chem. 26 (2012) 56–61.
[13] A. Zonouzi, M. Sadeghi Googheri, P. S. Miralinaghi, Org. Prep. Proced. Int. 40, (2008) 471-477.
[14] L.C. Rao, H.M. Meshram, N.S. Kumar, N.N. Rao, N.J. Babu, Tetrahedron Lett. 55 (2014) 1127–1131.
[15] G.M. Nazeruddin, M.S. Pandharpatte, K.B. Mulani, C.R. Chim. 15 (2012) 91-95.
[16] B. Karimi, H. Behzadnia, Catal. Commun. 12 (2011) 1432-1436.
[17] K.A. Parker, T.L. Mindt, Org. Lett. 3 (2001) 3875-3578.
[18] A. Shaabani, R. Ghadari, A. Sarvary, A.H. Rezayan, J. Org. Chem. 74 (2009) 4372-4374.
[19] T.B. Machado, A.V. Pinto, M.C.F.R. Pinto, I.C.R. Leal, M.G. Silva, A.C.F. Amaral, R.M. Kuster, K.R. Netto-dosSantos, Int. J. Antimicro. Ag. 21 (2003) 279-
284.
[20] R.V.A. Orru, E. Ruijter, Synthesis of Heterocycles via Multicomponent Reactions. Springer: Wurzburg,
2010.
[21] T.J.J. Muller, Multicomponent Reactions 1. Georg Thieme Verlag KG: Stuttgart, 2014.
[22] A. Shaabani, A.H. Rezayan, A. Sarvary, A. Rahmati, H.R. Khavasi, Catal. Commun. 9 (2008) 1082-1086.
[23] A. Shaabani, R. Ghadari, S. Ghasemi, M. Pedarpour, A.H. Rezavan, A. Sarvary, S.W. Ng, J. Comb. Chem. 11 (2009) 956-959.
[24] A. Shaabani, R. Ghadari, A. Rahmati, A.H. Rezayan, J. Iran. Chem. Soc. 6 (2009) 710-714.