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Organocatalytic Synthesis of N-Substituted 5-Arylidene Rhodanines
Corresponding Author(s) : N.S. Devi
Asian Journal of Chemistry,
Vol. 29 No. 3 (2017): Vol 29 Issue 3
Abstract
A simple and efficient synthesis of N-substituted 5-arylidene rhodanines has been developed via aldol condensation of N-substituted rhodanines with aromatic aldehydes using L-proline as the catalyst in water at room temperature. The attractive features of this protocol are simple experimental procedures, cleaner reactions, column free, high yield and avoid the use of toxic solvents.
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- M.W. Irvine, G.L. Patrick, J. Kewney, S.F. Hastings and S.J. MacKenzie, Bioorg. Med. Chem. Lett., 18, 2032 (2008).
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References
M.W. Irvine, G.L. Patrick, J. Kewney, S.F. Hastings and S.J. MacKenzie, Bioorg. Med. Chem. Lett., 18, 2032 (2008).
C. Nitsche, V.N. Schreier, M.A.M. Behnam, A. Kumar, R. Bartenschlager and C.D. Klein, J. Med. Chem., 56, 8389 (2013).
X.-Y. He, L. Lu, J. Qiu, P. Zou, F. Yu, X.-K. Jiang, L. Li, S. Jiang, S. Liu and L. Xie, Bioorg. Med. Chem. Lett., 21, 7539 (2013).
T.N. Reddy, M. Ravinder, P. Bagul, K. Ravikanti, C. Bagul, J.B. Nanubolu, K. Srinivas, S.K. Banerjee and V.J. Rao, Eur. J. Med. Chem., 71, 53 (2014).
M.J. Robertson, G. Hadzic, J. Ambrus, D.Y. Pomè, E. Hyde, A. Whiting, A. Mariana, L. von Kleist, N. Chau, V. Haucke, P.J. Robinson and A. McCluskey, J. Med. Chem. Lett., 3, 352 (2012).
W.T. Sing, C.L. Lee, S.L. Yeo, S.P. Lim and M.M. Sim, Bioorg. Med. Chem. Lett., 11, 91 (2001).
A. Ben-Alloum, S. Bakkas, K. Bougrin and M. Soufiaoui, New J. Chem., 22, 809 (1998).
K. Bourahla, A. Derdour, M. Rahmouni, F. Carreaux and J.P. Bazureau, Tetrahedron Lett., 48, 5785 (2007).
M. Radi, L. Botta, G. Casaluce, M. Bernardini and M. Botta, J. Comb. Chem., 12, 200 (2010).
N. Azizi, M. Hasani, M. Khajeh and M. Edrisi, Tetrahedron Lett., 56, 1189 (2015).
S. Gabillet, D. Lecercle, O. Loreau, M. Carboni, S. De’zard, J.M. Gomis and F. Taran, Org. Lett., 9, 3925 (2007).
K. Kumaravel and G. Vasuki, Curr. Org. Chem., 13, 1820 (2009).
Y. Gu, Green Chem., 14, 2091 (2012).
B. List, R.A. Lerner and C.F. Barbas III, J. Am. Chem. Soc., 122, 2395 (2000).
Y. Wang, Z. Shang, T. Wu, J. Fan and X. Chen, J. Mol. Catal. A: Chem., 253, 212 (2006).