Document Type: Original Research Article

Authors

1 Mumbai University, Mumbai

2 Mumbai University

3 Solapur University, Solapur

Abstract

An environmentally benign and clean synthesis of aryl-hydrazones by reacting variety of carbonyl compounds with thiosemicarbazide, semicarbazide, aminoguanidine, and phenyl hydrazine has been achieved using aqueous extract of Acacia concinna pods as a natural surfactant type catalyst. We found that the aqueous extract of Acacia concinna pods could be effectively used for the synthesis of aryl-hydrazones. This efficient process proceeds smoothly in aqueous medium at room temperature within a very short period of time. All the products were obtained by simple filtration. The low cost, easy availability of the catalyst and simple reaction conditions are the notable features of the present method.

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[1]         (a) L. Savini, P. Massarelli, L. Chiasserini, A. Sega, C. Pellerano, A. Barzi, G. Nocentini, Eur. J. Med. Chem., 1995, 30, 547-552; (b) S.M. Sondhi, M. Dinodia, A. Kumar, Bioorg. Med. Chem., 2006, 14, 4657-4663; (c) S.A. Khan, M. Yusuf, Eur. J. Med. Chem., 2009, 44, 2270-2274.

[2]         (a) A.A. Aly, A.A. Hassan, M.A. Ameen, Tetrahedron Lett., 2008, 49, 4060-4062; (b) T.M. Aquino, A.P. Liesen, R.E.A. Silva, V.T. Lima, C.S. Carvalho, A.R. Faria, J.M. Araújo, J.G. Lima, A.J. Alves, E.J.T. Melo, A.J.S. Góes, Bioorg. Med. Chem., 2008, 16, 446-456.

[3]         (a) R.F.F. Costa, A.P. Rebolledo, T. Matencio, H.D.R. Calado, J.D. Ardisson, M.E. Cortes, B.L. Rodrigues, H. Beraldo, J. Coord. Chem., 2005, 58, 1307-1319; (b) A.P. Rebolledo, M. Vieites, D. Gambino, O.E. Piro, E.E. Castellano, C.L. Zani, E.M. Souza-Fagundes, L.R. Teixeira, A.A. Batista, H. Beraldo, J. Inorg. Biochem., 2005, 99, 698-706.

[4]         (a) R.W. Brockman, J.R. Thomson, M.J. Bell, H.E. Skipper, Cancer Res., 1956, 16, 167-70; (b) D.J. Bauer, Br. Med. Bull. 1985, 41, 309-314; (c) H. Beraldo, D. Gambino, Mini-Rev. Med. Chem., 2004, 4, 31-39.

[5]         Y. Yen, K. Margolin, J. Doroshow, M. Fishman, B. Johnson, C. Clairmont, D. Sullivan, M.A. Sznol, Cancer Chemother. Pharmacol., 2004, 54, 331-342.

[6]         (a) P.T. Davidson, H.Q. Le, 1992, 43; 651; (b) E.A.B.M.R. Council, Tubercle 1963, 44, 301-333.

[7]         (a) S. Ren, R. Wang, K. Komatsu, B.K. Patricia, Y. Zyrianov, C.E. Mckenna, C. Csipke, Z.A. Tokes, E.J. Lien, J. Med Chem., 2002, 45, 410-419; (b) A. Andreani, M. Rambaldi, A. Leoni, A. Locatelli, R. Bossa, A. Fraccari, I. Galatulas, G. Salvatore, J. Med. Chem., 1996, 39, 2852-2855; (c) A. Das, M.D. Trousdale, S.J. Ren, E.J. Lien, Antiviral res., 1999, 44, 201-208.

[8]         (a) L. Savini, V. Travagli, C. Pellerano, E. Novellino, S. Cosentino, M.B. Pisano, Eur. J. Med. Chem., 2004, 39, 113-204; (b) P. Melnyk, V. Leroux, C. Sergheraert, P. Grellier, Bioorg. Med. Chem. Lett., 2006, 16, 31-35.

[9]         (a) M. Ramu, R. Nagarajan, Tetrahedron Lett., 2006, 47,  7557-7561; (b) B.K. Banik, K.J. Barakat, W.R. Wagle, M.S. Manhas, A.K. Bose, J. Org. Chem., 1999, 64, 5746-5753; (C) S. Cunha, T. Silva, Lima da, Tetrahedron Lett., 2009, 50, 2090-2093.

[10]     (a) M. Jes˘elnik, R.S. Varma, S. Polanc, M. Koc˘evar, Chem. Commun., 2001, 1716-1717; (b) M. Jes˘elnik, R.S. Varma, S. Polanc, M. Koc˘evar, Green. Chem., 2002, 4, 35-38.

[11]     V. Polshettiwar, R.S. Varma, Tetrahedron Lett., 2007, 48, 5649-5652.

[12]     A.C. Leite, D.R. Moreira, L.C. Coelho, F.D. Menezes, D.J. Brondani, Tetrahedron Lett., 2008, 49, 1538-1541.

[13]     (a) A. Alfermann, Biocatalysis in Organic Synthesis, ed. J. Tramper, H. Vander Plas, and P. Linko, Elsevier, Amsterdam, 1985, p. 25; (b) F. Baladassare, G. Bertoni, C. Chiappe, and F. Marioni, J. Mol. Catal. B: Enzym., 2000, 11, 55–58.

[14]     (a) J.S. Yadav, S. Nanda, P.T. Reddy,  and A.B. Rao, J. Org. Chem., 2002, 67, 3900-3903; (b) J.S. Yadav, P.T. Reddy, and S.R. Hashim, Synlett, 2000, 7, 1049-1051; (c) A. Chadha, M. Manohar, T. Soundararajan, and T.S. Lokeswari, Tetrahedron: Asymmetry, 1996, 7, 1571-1577; (d) B. Bhaskar, S. Ganesh, T.S. Lokeswari, A. Chadha, J. Mol. Catal. B: Enzym., 2004, 27, 13-18; (e) G. Kumarswamy, and S. Ramesh, Green Chem., 2003, 5, 306-308; (f) A.M. Fonseca, F.J.Q. Monte, M.F.C. de Oliveira, M.C. de Mattos, G.A. Cordell, R. Braz-Filho, T.L.G. Lemos,  J. Mol. Catal. B. Enzym., 2009, 57, 78-82.

[15]     G. Pratap, V.S. Bhaskar Rao, Fett Wissenschaft Technologie, 1987, 89, 205-208.

[16]     (a) A.S.R. Anjaneyulu, M. Bapuji, L.R. Rao, A. Sree, Phytochemistry, 1979, 18, 463-466; (b) M.A. Gafur, T. Obata, F. Kiuchi, Y. Tsuda, Chem. Pharm. Bull., 1997, 45, 620-625.

[17]     I.P. Varshney, K.M. Shamsuddin, Tetrahedron Lett., 1964, 5, 2055-2058.

[18]     I.P. Varshney, K.M. Shamsuddin, Bull. Chem. Soc. Japan., 1970, 43, 3830-3840.

[19]     (a) H.V. Chavan, B.P. Bandgar, ACS Sustainable Chem. Eng., 2013, 1, 929-936; (b) V.K. Tandon, H.M. Maurya, Tetrahedron Lett., 2010, 51, 3843-3846; (c) L-M. Wang, N. Jiao, Qiu, J-J. Yu, J-Q. Liu, F-L. Guo, Y. Liu, Tetrahedron, 2010, 66, 339-343.