Application of silica vanadic acid as a dual Lewis and Bronsted acid catalytic ability in Dakin West reaction

Document Type : Articles

Authors

1 Department of Medicinal Plants Production, Nahavand University, Nahavand, 6593139565, Iran.

2 Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran.

3 Pishro Parsian Company, 11th floor, No. 1917, Amir Bldg, above the four way the Jalal Alahmad, North Kargar Ave, PC: 1439713134, Tehran, Iran.

Abstract

Silica Vanadic Acid, SVA, (oxo-vanadium has been supported on silica) as a dual Lewis and Bronsted acid ability was prepared and efficiently catalyzed one-pot multi-component condensation of enolizable ketones or alkyl acetoacetates with aromatic aldehydes, acetonitrile and acetyl chloride. The described reaction was produced β-acetamido ketone or ester derivatives in high to excellent yields in relatively short reaction times in heterogeneous catalytic system at room temperature. Other advantages of this method is applicable at large scales without significant loss of the yields. In addition, this method is superior to reported methods, for the synthesis of β-acetamido ketone or ester derivatives.

Keywords


[1] M.R. Maurya, A. Kumar, J.C. Pessoa, Coord. Chem. Rev. 255 (2011) 2315-2344.
[2] E.F. Aboelfetoh, R. Pietschnig, Catal. Lett. 127 (2009) 83–94.
[3] S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron 65 (2009) 10155–10161.
[4] B. Ganem, Acc. Chem. Res. 42 (2009) 463–472.
[5] D. Enders, M. Moser, G. Geibel and M.C. Laufer, Synthesis (2004) 2040-2046.
[6] J. Barluenga, A.L. Viado, E. Aguilar, S. Fustero, B. Olano, J. Org. Chem. 58 (1993) 5972–5975.
[7] K. Kobinata. M. Uramoto, M. Nishii, H. Kusakabe, G. Nakamura, K. Isono, Agric. Biol. Chem. 44 (1980) 1709-1711.
[8] B. Das, M. Krishnaiah, K. Laxminarayana, K. Ravinder Reddy, J. Mol. Catal. A: Chem. 270 (2007) 284–288.
[9] D. Bahulayan, S.K. Das, J. Iqbal, J. Org. Chem. 68 (2003) 5735–5738.
[10] I.N. Rao, E.N. Prabhakaran, S.K. Das, J. Iqbal, J. Org. Chem. 68 (2003) 4079–4082.
[11] E.N. Prbhakaran, J. Iqbal, J. Org. Chem. 64 (1999) 3339–3341.
[12] B. Bhatia, M.M. Reddy, J. Iqbal, J. Chem. Soc. Chem. Commun. (1994) 713–714.
[13] M.M. Heravi, L. Ranjbar, F. Derikvand, F.F. Bamoharram, Catal. Commun. 8 (2007) 289-291.
[14] E. Rafiee, F. Shahbazi, M. Joshaghani, F. Tork, J. Mol. Catal. A: Chem. 242 (2005) 129– 134.
[15] R. Momeni, M. Sadeghi, Appl. Catal A 357 (2009) 100–105.
[16] H. Mao, J. Wan, Y. Pan, Tetrahedron 65 (2009) 1026-1032.
[17] R. Ghosh, S. Maity, A. Chakraborty, Synlett (2005) 115–118.
[18] B. Das, K.R. Reddy, R. Ramu, P. Thirupathi, B. Ravikanth, Synlett 11 (2006) 1756–1758.
[19] M.M. Khodaei, A.R. Khosropour, P. Fattahpour, Tetrahedron Lett. 46 (2005) 2105–2108.
[20] M.T. Maghsoodlou, A. Hassankhani, H.R. Shaterian, S.M. Habibi-Khorasani, E. Mosaddegh, Tetrahedron Lett. 48 (2007) 1729–1734.
[21] V.S. Shinu, B. Sheej, E. Purushothaman, D. Bahulayan, Tetrahedron Lett. 50 (2009) 4838–4843.
[22] M.M. Heravi, L. Ranjbar, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A: Chem. 276 (2007) 226-229.
[23] R. Ghosh, S. Maiti, A. Chakraborty, S. Chakraborty, A.K. Mukherjee, Tetrahedron 62 (2006) 4059–4064.
[24] M. Safaiee, M.A. Zolfigol, M. Tavasoli, M. Mokhlesi, J. Chem. Iran. Soc. 11 (2014) 1593-1597.
[25] M.A. Zolfigol, A. Khazaei, M. Safaiee, M. Mokhlesi, R. Rostamian, M. Bagheri, M. Shiri, H.G. Kruger, J. Mol. Catal. A: Chem. 370 (2013) 80-86.
[26] A. Khazaei, M.A. Zolfigol, M. Safaiee, M. Mokhlesi, E. Donyadari, M. Shiri, H. G. Kruger, Catal. Commun. 26 (2012) 34-38.
[27] G. Pandey, R.P. Singh, A. Garg, V.K. Singh, Tetrahedron Lett. 46 (2005) 2137–2140.
[28] M.A. Zolfigol, A. Khazaei, M. Mokhlesi, A. Zare, M. Safaiee, F. Derakhshan-Panah, H. Keypour, A.A. Dehghani-Firouzabadi, M. Merajoddin, Chin. J. Chem. 30 (2012) 345-352.
[29] L. Yu, B. Chen, X. Huang, Tetrahedron Lett. 48 (2007) 925-929.
[30] B. Das, R.A. Kumar, P. Thirupathi, Y. Srinivas, Synth. Commun. 39 (2009) 3305–3314.
[31] I. Nageshwar Rao, E.N. Prabhakaran, S. Kumar Das, J. Iqbal, J. Org. Chem. 68 (2003) 4079-4082.
[32] B.F. Mirjalili, M.M. Hashemi, B. Sadeghi, H. Emtiazi, J. Chin. Chem. Soc. 56 (2009) 386–391.
[33] A.T. Khan, L.H. Choudhury, T. Parvin, A.M. Asif, Tetrahedron Lett. 47 (2006) 8137-8141.
[34] F.K. Behbahani, N. Doragi, M.M. Heravi, Synth. Commun. 42 (2012) 705-713.
[35] A.T. Khan, T. Parvin, L.H. Choudhury, Tetrahedron 63 (2007) 5593-5601.
[36] A.K. Tiwari, R.M. Kumbhare, S.B. Agawane, A.Z. Ali, K.V. Kumar, Bioorg. Med. Chem. Lett. 18 (2008) 4130-4132.