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Alum-Cs2CO3 as a New Recyclable Solid Base Catalyst for the Efficient Syntheses of Arylidenemalononitriles, Esters and Arylcinnamic Acids in Water
Corresponding Author(s) : Ashok Kumar Taduri
Asian Journal of Chemistry,
Vol. 26 No. 7 (2014): Vol 26 Issue 7
Abstract
The condensation between aromatic aldehydes and malononitrile, ethylcyanoacetate and malonic acid for the syntheses of arylidenemalononitriles, arylidenemalonic acid esters and aryl cinnamic acids in water using alum-Cs2CO3 as a solid support catalyst has been described. Alum-Cs2CO3 was found to be a highly active, stable and recyclable catalyst under reaction conditions.
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- C. Pellerin, Chemistry Goes Green, In E-journal USA; Global Issues, June (2005).
- C.J. Li, Chem. Rev., 93, 2023 (1993); doi:10.1021/Cr00022a004.
- J. Azizian, A.A. Mohammadi, I. Bidar and P. Mirzaei, Monatsh. Chem., 139, 805 (2008); doi:10.1007/S00706-007-0833-9.
- D. Suresh Kumar and S.J. Sandhu, Indian J. Chem., 50B, 1479 (2011).
- K.F. Shelke, S.B. Sapkal, G.K. Kakade, S.A. Sadaphal, B.B. Shingate and M.S. Shingare, Green Chem. Lett. Rev., 3, 17 (2010); doi:10.1080/17518250903478345.
- A. Mobinikhaledi, N. Foroughifar and M.A.B. Fard, Synth. React. Inorg., Metal-Org. Nano-Metal Chem., 40, 179 (2010); doi:10.1080/15533171003629121.
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- C. Wiener, C.H. Schroeder and K.P. Link, J. Am. Chem. Soc., 79, 5301 (1957); doi:10.1021/Ja01576a059.
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- P. De, M. Baltas and F. Bedos-Belval, Curr. Med. Chem., 18, 1672 (2011); doi:10.2174/092986711795471347.
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- T. Pyysalo, H. Torkkeli and E. Honkanen, Lebenson. Wiss. Technol., 10, 145 (1977).
- B.M. Choudary, M. Lakshmi Kantam, B. Kavita, C. Venkat Reddy and F. Figueras, Tetrahedron, 56, 9357 (2000); doi:10.1016/S0040-4020(00)00906-6.
- S. Balalaie and N. Nemati, Synth. Commun., 30, 869 (2000); doi:10.1080/00397910008087099.
- Y.Q. Cao, Z. Dai, R. Zhang and B.H. Chen, Synth. Commun., 34, 2965 (2004); doi:10.1081/SCC-200026650.
- R.H. Khan, R.K. Mathur and A.C. Ghosh, Synth. Commun., 26, 683 (1996); doi:10.1080/00397919608086741.
- X. Fan, X. Hu, X. Zhang and J. Wang, Aust. J. Chem., 57, 1067 (2004); doi:10.1071/CH04060.
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- R. Wojciechowska, W. Wojciechowski and J. Kamiński, J. Themal Anal., 33, 503 (1988); doi:10.1007/BF01913929.
- M. Feroci, M. Orsini, L. Palombi and A. Inesi, Green Chem., 9, 323 (2007); doi:10.1039/B614483g.
- J.H. Buckingham, Dictionary of Organic Compounds, edn 5, Vol. 1, p. 1195 (1982).
References
C. Pellerin, Chemistry Goes Green, In E-journal USA; Global Issues, June (2005).
C.J. Li, Chem. Rev., 93, 2023 (1993); doi:10.1021/Cr00022a004.
J. Azizian, A.A. Mohammadi, I. Bidar and P. Mirzaei, Monatsh. Chem., 139, 805 (2008); doi:10.1007/S00706-007-0833-9.
D. Suresh Kumar and S.J. Sandhu, Indian J. Chem., 50B, 1479 (2011).
K.F. Shelke, S.B. Sapkal, G.K. Kakade, S.A. Sadaphal, B.B. Shingate and M.S. Shingare, Green Chem. Lett. Rev., 3, 17 (2010); doi:10.1080/17518250903478345.
A. Mobinikhaledi, N. Foroughifar and M.A.B. Fard, Synth. React. Inorg., Metal-Org. Nano-Metal Chem., 40, 179 (2010); doi:10.1080/15533171003629121.
S.S. Swapnil, A.S. Sandip, H.K. Amol, U.P. Rajkumar, B.S. Bapurao and S.S. Murlidhar, Bull. Korean Chem. Soc., 30, 825 (2009); doi:10.5012/Bkcs.2009.30.4.825.
J. Azizian, A.A. Mohammadi, A.R. Karimi and M.R. Mohammadizadeh, Appl. Catal. A, 300, 85 (2006); doi:10.1016/j.apcata.2005.11.001.
J.A. Cabello, J.M. Campelo, A. Garcia, D. Luna and J.M. Marinas, J. Org. Chem., 49, 5195 (1984); doi:10.1021/Jo00200a036.
(a) P. Shanthan Rao and R.V. Venkataratnam, Tetrahedron Lett., 32, 5821 (1991); doi:10.1016/S0040-4039(00)93564-0; (b) D. Prajapati, K.C. Lekhok, J.S. Sandhu And A.C. Ghosh, J. Chem. Soc. Perkin Trans, 959 (1996); doi:10.1039/P19960000959; (c) D. Prajapati and J.S. Sandhu, J. Chem. Soc. Perkin Trans., 739 (1993); doi:10.1039/P19930000739; (d) Y.Q. Li, J. Chem. Res. (S), 524 (2000); doi:10.3184/030823400103166003; (e) N. Iranpoor, B. Zeynizadeh And A. Aghapour, J. Chem. Res. (S), 9, 554 (1999); doi:10.1039/A809827a.; (f) X.Y. Zhang, X.S. Fan, H.Y. Niu And J. Wang, J. Green Chem., 5, 267 (2003); doi:10.1039/B212155g; (g) N. Iranpoor And F. Kazemi, Tetrahedron, 54, 9475 (1998); doi:10.1016/S0040-4020(98)00575-4; (h) L. Wang, J. Sheng, H. Tian, J. Han, Z. Fan And C.A. Qian, Synthesis, 3060 (2004); doi:10.1055/S-2004-834900.; (i) P. Salehi, M. Dabiri, M.A. Zolfigol and M.A.B. Fard, J. Braz. Chem. Soc., 15, 773 (2004); doi:10.1590/S0103-50532004000500026.; (j) Q.L. Wang, Y. Ma and B. Zuo, Synth. Commun., 27, 4107 (1997); doi:10.1080/00397919708005458.; (k) T.I. Reddy and R.S. Varma, Tetrahedron Lett., 38, 1721 (1997); doi:10.1016/S0040-4039(97)00180-9.; (l) Y. Lu, Z. Ren, W. Cao, W. Tong and M. Gao, Synth. Commun., 34, 2047 (2004); doi:10.1081/SCC-120037918.; (m) J.T. Li, G.F. Chen, S.X. Wang, L. He and T.S. Li, Aust. J. Chem., 58, 231 (2005); doi:10.1071/CH03308.; (n) H. Moison, F. Texier-Boullet and A. Foucaud, Tetrahedron, 43, 537 (1987); doi:10.1016/S0040-4020(01)89986-5.; (o) F. Freeman, Chem. Rev., 80, 329 (1980); doi:10.1021/Cr60326a004.
(A) L.F. Tietze, Chem. Rev., 96, 115 (1996); doi:10.1021/Cr950027e.; (B) H.A. Oskooie, M.M. Heravi, F. Derikvand, M. Khorasani and F.F. Bamoharram, Synth. Commun., 36, 2819 (2006); doi:10.1080/00397910600770631.; (C) J. Quiroga, M. Alvarado, B. Insuasty, R. Moreno, E. Raviña, I. Estevez and R.H. De Almeida S, J. Heterocycl. Chem., 36, 1311 (1999); doi:10.1002/Jhet.5570360533.
C. Wiener, C.H. Schroeder and K.P. Link, J. Am. Chem. Soc., 79, 5301 (1957); doi:10.1021/Ja01576a059.
T.L.V. Ulbricht, T. Okuda and C.C. Prince, In Organic Syntheses, Collective,Vol 4. John Wiley & Sons, New York, p. 566 (1963).
P. De, M. Baltas and F. Bedos-Belval, Curr. Med. Chem., 18, 1672 (2011); doi:10.2174/092986711795471347.
P. De, G. Koumba Yoya, P. Constant, F. Bedos-Belval, H. Duran, N. Saffon, M. Daffé and M. Baltas, J. Med. Chem., 54, 1449 (2011); doi:10.1021/Jm101510d.
T. Pyysalo, H. Torkkeli and E. Honkanen, Lebenson. Wiss. Technol., 10, 145 (1977).
B.M. Choudary, M. Lakshmi Kantam, B. Kavita, C. Venkat Reddy and F. Figueras, Tetrahedron, 56, 9357 (2000); doi:10.1016/S0040-4020(00)00906-6.
S. Balalaie and N. Nemati, Synth. Commun., 30, 869 (2000); doi:10.1080/00397910008087099.
Y.Q. Cao, Z. Dai, R. Zhang and B.H. Chen, Synth. Commun., 34, 2965 (2004); doi:10.1081/SCC-200026650.
R.H. Khan, R.K. Mathur and A.C. Ghosh, Synth. Commun., 26, 683 (1996); doi:10.1080/00397919608086741.
X. Fan, X. Hu, X. Zhang and J. Wang, Aust. J. Chem., 57, 1067 (2004); doi:10.1071/CH04060.
L.F. Tietze, U. Beifuss and B. Trost, In Comprehensive Organic Synthesis, Pergamon Press, Oxford, Vol. 2, p. 341 (1991).
G. Jones, Org. React., 15, 704 (1967).
R. Wojciechowska, W. Wojciechowski and J. Kamiński, J. Themal Anal., 33, 503 (1988); doi:10.1007/BF01913929.
M. Feroci, M. Orsini, L. Palombi and A. Inesi, Green Chem., 9, 323 (2007); doi:10.1039/B614483g.
J.H. Buckingham, Dictionary of Organic Compounds, edn 5, Vol. 1, p. 1195 (1982).