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An Efficient and Eco-Friendly Solvent-Free Synthesis of β-Acetamido Ketones Using L-Proline As a Green and Reusable Catalyst
Corresponding Author(s) : M. Roshani
Asian Journal of Chemistry,
Vol. 25 No. 4 (2013): Vol 25 Issue 4
Abstract
A simple and efficient catalytic protocol for the synthesis of b-acetamido ketones via the one-pot, four component condensation of aryl aldehydes, enolizable aryl ketones, acetyl chloride and acetonitrile using L-proline is reported. The present method offers several advantages such as high yields, short reaction times, recovery and reusability of catalyst and easy workup procedures.
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- A.S. Bommarus and K.M. Polizzi, Chem. Eng. Sci., 61, 1004 (2006).
- P.I. Dalko and L. Moisan, Angew. Chem. Int. Ed., 43, 5138 (2004).
- S. Vijaikumar, A. Dhakshinamoorthy and K. Pitchumani, Appl. Catal., 340, 25 (2008).
- A.B. Northrup and D.W.C. MacMillan, J. Am. Chem. Soc., 124, 6798 (2002).
- A. Cordova, Acc. Chem. Res., 37, 102 (2004).
- D. Enders and A. Seki, Synlett, 26 (2002).
- T. Bui and C.F. Barbas, Tetrahedron Lett., 41, 6951 (2000).
- A. Cordova, W. Notz, G. Zhong, J. Betancort and C.F. Barbas III, J. Am. Chem. Soc., 124, 1842 (2002).
- R.O. Duthaler, Angew Chem. Int. Ed., 42, 975 (2003).
- Y. Hayashi, J. Yamaguchi and T. Sumiya, Angew. Chem. Int. Ed., 43, 1112 (2004).
- N. Vihnola and B. List, J. Am. Chem. Soc., 126, 450 (2004).
- J.R. Casimir, C. Turetta, L. Ettouati and J. Paris, Tetrahedron Lett., 36, 4797 (1995).
- A.G. Godfrey, D.A. Brooks, L.A. Hay, M. Peters, J.R. McCarthy and D. Mitchell, J. Org. Chem., 68, 2623 (2003).
- D. Enders, M. Moser, G. Geibel and M.C. Laufer, Synthesis, 2040 (2004).
- K. Kobinata, M. Uramoto, M. Nishii, H. Kusakabe, G. Nakamura and K. Isono, Agric. Biol. Chem., 44, 1709 (1980).
- P. Dallemagne, S. Rault, H. Cugnon de Sévricourt, Kh.M. Hassan and M. Robba, Tetrahedron Lett., 27, 2607 (1986).
- P.W. Jeffs, R. Redfearn and J. Wolfram, J. Org. Chem., 48, 3861 (1983).
- M.R. Paleo, D. Domínguez and L. Castedo, Tetrahedron Lett., 34, 2369 (1993).
- I.N. Rao, E.N. Prabhakaran, S.K. Das and J. Iqbal, J. Org. Chem., 68, 4079 (2003).
- E.N. Prabhakaran and J. Iqbal, J. Org. Chem., 64, 3339 (1999).
- M.M. Khodaei, A.R. Khosropour and P. Fattahpour, Tetrahedron Lett., 46, 2105 (2005).
- G.R. Pandey, R.P. Singh, A. Garg and V.K. Singh, Tetrahedron Lett., 46, 2137 (2005).
- R.P. Bhat, V.P. Raje, V.M. Alexander, S.B. Patil and S.D. Samant, Tetrahedron Lett., 46, 4801 (2005).
- B. Das, K. Ravinder Reddy, R. Ramu, P. Thirupathi and B. Ravikanth, Synlett, 1756 (2006).
- R. Ghosh, S. Maity and A. Chakraborty, Synlett, 115 (2005).
- R. Ghosh, S. Maiti,A. Chakraborty, S. Chakraborty and A.K. Mukherjee, Tetrahedron, 62, 4059 (2006).
- L. Nagarapu, S. Kantevari, V.N. Cheemalapati, S. Apuri and N.V. Kumari, J. Mol. Catal. A, 264, 22 (2007).
References
A.S. Bommarus and K.M. Polizzi, Chem. Eng. Sci., 61, 1004 (2006).
P.I. Dalko and L. Moisan, Angew. Chem. Int. Ed., 43, 5138 (2004).
S. Vijaikumar, A. Dhakshinamoorthy and K. Pitchumani, Appl. Catal., 340, 25 (2008).
A.B. Northrup and D.W.C. MacMillan, J. Am. Chem. Soc., 124, 6798 (2002).
A. Cordova, Acc. Chem. Res., 37, 102 (2004).
D. Enders and A. Seki, Synlett, 26 (2002).
T. Bui and C.F. Barbas, Tetrahedron Lett., 41, 6951 (2000).
A. Cordova, W. Notz, G. Zhong, J. Betancort and C.F. Barbas III, J. Am. Chem. Soc., 124, 1842 (2002).
R.O. Duthaler, Angew Chem. Int. Ed., 42, 975 (2003).
Y. Hayashi, J. Yamaguchi and T. Sumiya, Angew. Chem. Int. Ed., 43, 1112 (2004).
N. Vihnola and B. List, J. Am. Chem. Soc., 126, 450 (2004).
J.R. Casimir, C. Turetta, L. Ettouati and J. Paris, Tetrahedron Lett., 36, 4797 (1995).
A.G. Godfrey, D.A. Brooks, L.A. Hay, M. Peters, J.R. McCarthy and D. Mitchell, J. Org. Chem., 68, 2623 (2003).
D. Enders, M. Moser, G. Geibel and M.C. Laufer, Synthesis, 2040 (2004).
K. Kobinata, M. Uramoto, M. Nishii, H. Kusakabe, G. Nakamura and K. Isono, Agric. Biol. Chem., 44, 1709 (1980).
P. Dallemagne, S. Rault, H. Cugnon de Sévricourt, Kh.M. Hassan and M. Robba, Tetrahedron Lett., 27, 2607 (1986).
P.W. Jeffs, R. Redfearn and J. Wolfram, J. Org. Chem., 48, 3861 (1983).
M.R. Paleo, D. Domínguez and L. Castedo, Tetrahedron Lett., 34, 2369 (1993).
I.N. Rao, E.N. Prabhakaran, S.K. Das and J. Iqbal, J. Org. Chem., 68, 4079 (2003).
E.N. Prabhakaran and J. Iqbal, J. Org. Chem., 64, 3339 (1999).
M.M. Khodaei, A.R. Khosropour and P. Fattahpour, Tetrahedron Lett., 46, 2105 (2005).
G.R. Pandey, R.P. Singh, A. Garg and V.K. Singh, Tetrahedron Lett., 46, 2137 (2005).
R.P. Bhat, V.P. Raje, V.M. Alexander, S.B. Patil and S.D. Samant, Tetrahedron Lett., 46, 4801 (2005).
B. Das, K. Ravinder Reddy, R. Ramu, P. Thirupathi and B. Ravikanth, Synlett, 1756 (2006).
R. Ghosh, S. Maity and A. Chakraborty, Synlett, 115 (2005).
R. Ghosh, S. Maiti,A. Chakraborty, S. Chakraborty and A.K. Mukherjee, Tetrahedron, 62, 4059 (2006).
L. Nagarapu, S. Kantevari, V.N. Cheemalapati, S. Apuri and N.V. Kumari, J. Mol. Catal. A, 264, 22 (2007).