Microwave-assisted Knoevenagel condensation of ethyl cyanoacetate with aldehydes in solvent-free condition

Journal of the Indian Chemical Society

Volumn 80, Issue 10, 2003, Pages 921-922

  Mitra, Alok Kumar ^a   Banerjee, Sajal Kumar ^a   Chattopadhyay, Sarmishtha ^a  

^a UNIVERSITY OF CALCUTTA   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; ALDEHYDE; PIPERAZINE; SOLVENT;

ANALYTIC METHOD; ARTICLE; CATALYST; CHEMICAL REACTION; KNOEVENAGEL CONDENSATION; MICROWAVE RADIATION; STRUCTURE ANALYSIS;

EID: 1842812855     PISSN: 00194522     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. B. M. Trost, "Comprehensive Organic Synthesis", Pergamon Press, Oxford, 1991, Vol. 2, p. 133; A. Hassner and C. Stumer, "Organic Syntheses Based on Name Reactions and Unnamed Reactions", Elsevier Science Inc., New York, 1st. ed., 1994, p. 205.
2. B. M. Trost, "Comprehensive Organic Synthesis", Pergamon Press, Oxford, 1991, Vol. 2, p. 133; A. Hassner and C. Stumer, "Organic Syntheses Based on Name Reactions and Unnamed Reactions", Elsevier Science Inc., New York, 1st. ed., 1994, p. 205.
3. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
4. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
5. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
6. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
7. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
8. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
9. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
10. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
11. S. Abdallah-El Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 259; F. Delgado, J. Tamarij, G. Zepeda, M. Landa, R. Miranda and J. Garcia, Synth. Commun., 1995, 25, 753; J-K. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and J-W. Lee, Synth. Commun., 1996, 26, 535; S-Y. Kim, P-S. Kwon, T-W. Kwon, S-K. Chung and Y-T. Chang, Synth. Commun., 1997, 27, 533; G. Sabitha, B. Y. S. Reddy, R. S. Babu and J. S. Yadav, Chem. Lett., 1998, 773; A. K. Shukla, S. Singh and K. N. Singh, Indian J. Chem., Sect. B, 2001, 40, 391; Y. Peng, G. Song and X. Qian, J. Chem. Res. (S), 2001, 188; N. Karchaudhuri, A. De and A. K. Mitra, J. Chem. Res. (S), 2002, 180; S. Sebti, A. Smahi and A. Solhy, Tetrahedron Lett., 2002, 43, 1813.
12. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
13. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
14. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
15. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
16. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
17. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
18. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
19. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
20. A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18; R. S. Varma, Green Chem., 1999, 43; A. K. Mitra, A. De and N. Karchaudhuri, Synth. Commun., 1999, 29, 573; J. Chem., Res. (S), 1999, 246; N-F Kaiser, U. Bremberg, M. Larhead, C. Moberg and A. Hallberg, Angew. Chem. Int. Ed. Engl., 2000, 39, 3596; M. R. Linder and J. Podlech, Org. Lett., 2001, 3, 1849; P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; B. L. Hayes, "Microwave Synthesis", CEM Publishihg, Matthews, 2002; J. C. Lee, H. J. Choi and Y. C. Lee, Tetrahedron Lett., 2003, 44, 123.
21. M. W. Toussaint, A. B. Rosencrance, L. M. Brennan, J. R. Beaman, M. J. Wolfe, F. J. Hoffmann and H. S. Gardner (Jr.), Environ. Health Perspec., 2001, 109, 35.
22. A. K. Mitra, A. De and N. Karchaudhuri, Synlett, 1998, 1345; J. Chem. Res. (S), 1999, 320, 560; Synth. Commun., 1999, 29, 2731; 2000, 30, 1651; K. Banerjee and A. K. Mitra, J. Indian Chem. Soc., 2003, 80, 51; A. K. Mitra and K. Banerjee, Synlett, 2003, 1509.
23. A. K. Mitra, A. De and N. Karchaudhuri, Synlett, 1998, 1345; J. Chem. Res. (S), 1999, 320, 560; Synth. Commun., 1999, 29, 2731; 2000, 30, 1651; K. Banerjee and A. K. Mitra, J. Indian Chem. Soc., 2003, 80, 51; A. K. Mitra and K. Banerjee, Synlett, 2003, 1509.
24. A. K. Mitra, A. De and N. Karchaudhuri, Synlett, 1998, 1345; J. Chem. Res. (S), 1999, 320, 560; Synth. Commun., 1999, 29, 2731; 2000, 30, 1651; K. Banerjee and A. K. Mitra, J. Indian Chem. Soc., 2003, 80, 51; A. K. Mitra and K. Banerjee, Synlett, 2003, 1509.
25. A. K. Mitra, A. De and N. Karchaudhuri, Synlett, 1998, 1345; J. Chem. Res. (S), 1999, 320, 560; Synth. Commun., 1999, 29, 2731; 2000, 30, 1651; K. Banerjee and A. K. Mitra, J. Indian Chem. Soc., 2003, 80, 51; A. K. Mitra and K. Banerjee, Synlett, 2003, 1509.
26. A. K. Mitra, A. De and N. Karchaudhuri, Synlett, 1998, 1345; J. Chem. Res. (S), 1999, 320, 560; Synth. Commun., 1999, 29, 2731; 2000, 30, 1651; K. Banerjee and A. K. Mitra, J. Indian Chem. Soc., 2003, 80, 51; A. K. Mitra and K. Banerjee, Synlett, 2003, 1509.
27. A. K. Mitra, A. De and N. Karchaudhuri, Synlett, 1998, 1345; J. Chem. Res. (S), 1999, 320, 560; Synth. Commun., 1999, 29, 2731; 2000, 30, 1651; K. Banerjee and A. K. Mitra, J. Indian Chem. Soc., 2003, 80, 51; A. K. Mitra and K. Banerjee, Synlett, 2003, 1509.