The Biginelli condensation: A novel and efficient regioselective synthesis of dihydropyrimidin-2(1H)-ones using lithium bromide

Chemistry Letters

Volumn , Issue 10, 2002, Pages 1038-1039

  Baruah, Partha P ^a   Gadhwal, Sunil ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ESTER DERIVATIVE; LITHIUM BROMIDE; LITHIUM DERIVATIVE; PYRIMIDINE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; POLYMERIZATION; SYNTHESIS;

EID: 0037027286     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.1038     Document Type: Article

References (23)

1. a) P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
2. b) C. O. Kappe, Tetrahedron, 49, 6937 (1993).
3. c) P. Wipf and A. Cunningham, Tetrahedron Lett., 36, 7819 (1995).
4. d) A. Studer, P. Jager, P. Wipf, and D. P. Curran, J. Org. Chem., 62, 2917 (1997).
5. a) K. S. Atwal, G. C. Rovnyak, B. C. O'Relly, and J. Schwartz, J. Org. Chem., 54, 5898 (1989).
6. b) K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg, and B. C. O'Relly, J. Med. Chem., 34, 806 (1991).
7. c) G. C. Rovnyak, K. S. Atwal, A. Hedberg, S. D. Kimball, S. Moreland, J. Z. Gougoutoy, B. C. O'Relly, J. Schwartz, and M. F. Malley, J. Med. Chem., 35, 3254 (1992).
8. d) C. O. Kappe, W. M. F. Fabian, Tetrahedron, 53, 2803 (1997).
9. L. E. Overman, M. H. Rabinowitz, and P. A. Renhowe, J. Am. Chem. Soc., 117, 2657 (1995).
10. a) A. D. Patil, N. V. Kumar, W. C. Kokke, M. F. Ben, A. J. Freyer, C. DeBrosse, S. Mai, A. Truneh, D. J. Faulkner, B. Carte, A. L. Breen, R. P. Hertzberg, R. K. Johnson, J. W. Westley, and B. C. M. Ports, J. Org. Chem., 60, 1182 (1995).
11. b) B. Snider, J. Chen, A. D. Patial, and A. Freyer, Tetrahedron Lett., 37, 6977 (1996).
12. c) A. V. R. Rao, M. K. Gurjar, and J. Vasudevan, J. Chem. Soc., Chem. Commun., 1995, 1369.
13. a) K. Folkers, H. J. Harwood, and T. B. Johnson, J. Am. Chem. Soc., 54, 3751 (1932).
14. b) S. I. Zavyalov and L. B. Kulikova, Khim.-Farm. Zh., 126, 116 (1992).
15. c) R. Gupta, A. K. Gupta, S. Paul, and P. L. Kachroo, Ind. J. Chem., 34B, 151 (1995).
16. d) E. H. Hu, D. R. Sidler, U. H. Dolling, and M. A. Patane, PCT Int. Appl. WO 97 21,687 (C1. C 07 D 239/36) 19 June 1997; Chem. Abstr., 127, 121750v (1997).
17. For a study of the pH dependence of the reaction see: A. Elison and Karimullah, Pak. J. Sci. Int. Res., 66, 83 (1967).
18. E. H. Hu, D. R. Sidler, and U. H. Dolling, J. Org. Chem., 63, 3454 (1998).
19. F. Bigi, S. Carloni, B. Frullanti, R. Maggi, and G. Sartori, Tetrahedron Lett., 40, 3465 (1999).
20. B. C. Ranu, A. Hajra, and U. Jano, J. Org. Chem., 65, 6270 (2000).
21. C. O. Kappe and S. F. Falsone, Synlett., 1998, 718.
22. For a very recent report see: K. A. Kumar, M. Kasthuraiah, C. S. Reddy, and C. D. Reddy, Tetrahedron Lett., 42, 7873 (2001).
23. K. Folkers, H. J. Harwood, and T. B. Johnson, J. Am. Chem. Soc., 54, 3751 (1932).