A novel L-proline catalyzed Biginelli reaction: One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions

Chemistry Letters

Volumn 33, Issue 9, 2004, Pages 1168-1169

  Yadav, J S ^a   Praveen Kumar, S ^a   Kondaji, G ^a   Srinivasa Rao, R ^a   Nagaiah, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2(1H) ONE DERIVATIVE; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; PROLINE; PYRIMIDINE DERIVATIVE; SOLVENT; THIOUREA; UNCLASSIFIED DRUG; UREA;

ARTICLE; BIGINELLI REACTION; CATALYSIS; POLYMERIZATION; SYNTHESIS;

EID: 9344260831     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1168     Document Type: Article

References (32)

1. a) Review: C. O. Kappe, Tetrahedron, 49, 6937 (1993).
2. b) Review: C. O. Kappe, Acc. Chem. Res., 33, 879 (2000).
3. c) Review: C. O. Kappe, Eur. J. Med. Chem., 35, 1043 (2000).
4. a) K. S. Atwal, G. C. Rovnyak, B. C. O'Reilly, and J. Schwartz, J. Org. Chem., 54, 5898 (1989).
5. b) G. J. Grover, S. Dzwonczyk, D. M. McMullen, D. E. Normandin, C. S. Arham, P. G. Sleph, and S. Moreland, J. Cardiovasc. Pharmacol., 26, 289 (1995) and references cited therein.
6. a) C. O. Kappe, W. M. F. Fabian, and M. A. Semones, Tetrahedron, 53, 2803 (1997).
7. b) J. C. Barrow, P. G. Nantermet, H. G. Selnick, K. L. Glass, K. E. Kittle, R. M. Freidinger, R. W. Ransom, S. S. O'Malley, P. Eppert, D. Nagarathnam, and C. Forray, J. Med. Chem., 43, 2703 (2000) and references cited therein.
8. a) B. B. Snider and Z. Shi, J. Org. Chem., 58, 3828 (1993) and references cited therein.
9. b) L. E. Overman, M. H. Rabinowitz, and P. A. Renhowe, J. Am. Chem. Soc., 117, 2657 (1995).
10. c) Review: L. Heys, C. G. Moore, and P. Murphy, Chem. Soc. Rev., 29, 57 (2000).
11. a) A. D. Patil, N. V. Kumar, W. C. Kokke, M. F. Bean, A. J. Freyer, C. De Brosse, S. Mai, A. Truneh, and D. Faulkner, J. Org. Chem., 60, 1182 (1995).
12. b) A. V. Rama Rao, M. K. Gurjar, and J. Vasudevan, J. Chem. Soc., Chem. Commun., 1995, 1369.
13. B. B. Snider, J. Chen, A. D. Patil, and A. Freyer, Tetrahedron Lett., 37, 6977 (1996).
14. a) T. U. Mayer, T. M. Kapoor, S. J. Haggarty, R. W. King, S. L. Screiber, and T. J. Mitchison, Science, 286, 971 (1999).
15. b) S. J. Haggarty, T. U. Mayer, D. T. Miyamoto, R. Fathi, R. W. King, T. J. Mitchison, and S. L. Screiber, Chem. Biol., 7, 275 (2000).
16. a) P. Biginelli, Ber., 24, 1317 (1891).
17. b) P. Biginelli, Ber., 26, 447 (1893).
18. c) P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
19. a) J. Barluenga, M. Tomas, A. Ballesteros, and L. A. Lopez, Tetrahedron Lett., 30, 4573 (1989).
20. b) K. S. Atwal, G. C. Rovnyak, B. C. O'Reilly, and J. Schwartz, J. Org. Chem., 54, 5898 (1989).
21. a) B. C. O'Reilly and K. S. Atwal, Heterocycles, 26, 1185 (1987).
22. b) K. R. Reddy, Ch. V. Reddy, M. Mahesh, P. V. K. Raju, and V. V. N. Reddy, Tetrahedron Lett., 44, 8173 (2003).
23. a) Review: C. O. Kappe, Tetrahedron, 49, 6937 (1993).
24. b) A. Shaabani, A. Bazgir, and F. Teimouri, Tetrahedron Lett., 44, 857 (2003) and references cited therein.
25. c) J. T. Li, J. F. Han, J. H. Yang, and T. S. Li, Ultrason. Sonochem., 10, 119 (2003).
26. d) D. Alessandro, M. Alessandro, S. Simona, and B. Valerio, J. Org. Chem., 67, 6979 (2003).
27. e) D. Alessandro, M. Alessandro, M. Erik, S. Simona, and B. Valerio, J. Org. Chem., 67, 6172 (2003).
28. B. List, Synlett, 2001, 1675 and references cited therein.
29. a) A. Bogevig, N. Kumaragurubaran, K. Juhl, W. Zhuang, and K. A. Jorgensen, Angew. Chem., Int. Ed. Engl., 41, 1790 (2002).
30. b) N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bogevig, and K. A. Jorgensen, J. Am. Chem. Soc., 124, 6254 (2002).
31. c) B. List, J. Am. Chem. Soc., 124, 5656 (2002).
32. B. List, P. Pojarliev, W. T. Biller, and H. J. Martin, J. Am. Chem. Soc., 124, 827 (2002).