N-bromosuccinimide as an almost neutral catalyst for efficient synthesis of dihydropyrimidinones under microwave irradiation

Synthesis

Volumn , Issue 8, 2004, Pages 1239-1242

  Hazarkhani, Hassan ^a   Karimi, Babak ^a  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

Author keywords

Dihydropyrimidinones; Microwave irradiation; N bromosuccinimide

Indexed keywords

DERIVATIVES; MICROWAVES; SYNTHESIS (CHEMICAL);

MICROWAVE IRRADIATION; NEUTRAL CATALYSTS;

CATALYSTS;

ANTIHYPERTENSIVE AGENT; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; CALCIUM CHANNEL BLOCKING AGENT; N BROMOSUCCINIMIDE; PYRIMIDINONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 2942700059     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822348     Document Type: Article

References (29)

1. (a) Cho, H.; Ueda, M.; Shima, K.; Mizuno, A.; Hayashimatsu, M.; Ohnaka, Y.; Takeuchi, Y.; Hamaguchi, M.; Aisaka, K.; Hidaka, T.; Kawai, M.; Takeda, M.; Ishihara, T.; Funahashi, K.; Satah, F.; Morita, M.; Noguchi, T. J. Med. Chem. 1989, 32, 2399.
2. (b) Atwal, K. S.; Rovnyak, G. C.; Kimball, S. D.; Floyd, D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, J. Z.; Schwartz, J.; Smillie, K. M.; Malley, M. F. J. Med. Chem. 1990, 33, 2629.
3. (c) Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; Dimarco, J. D.; Gougoutas, J.; Hedberg, A. Ó.; Malley, M.; McCarthy, J. P.; Zhang, R.; Moreland, S. J. Med. Chem. 1995, 38, 119.
4. (a) Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A. Ó.; Reilly, B. C. J. Med. Chem. 1991, 34, 806.
5. (b) Grover, G. J.; Dzwonczyk, S.; McMullen, D. M.; Normadinam, C. S.; Sleph, P. G.; Moreland, S. J. J. Cardiovasc. Pharmacol. 1995, 26, 289.
6. Snider, B. B.; Shi, Z. J. Org. Chem. 1993, 58, 3823.
7. (a) Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; De Brosse, C.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westly, J. W.; Potts, B. C. M. J. Org. Chem. 1995, 60, 1182.
8. (b) Rama Rao, A. V.; Gujar, M. K.; Vasudevan, J. J. Chem. Soc., Chem. Commun. 1995, 1369.
9. (c) Snider, B. B.; Chen, J.; Patil, A. D.; Freyer, A. Tetrahedron Lett. 1996, 37, 6977.
10. (a) Biginelli, P. Gazz. Chem. Ital. 1893, 23, 360.
11. (b) For a review see also: Kappe, C. O. Tetrahedron 1993, 49, 6937.
12. Fu, N. Y.; Yuan, Y. F.; Cao, Z.; Wang, S. W.; Wang, J. T.; Peppe, C. Tetrahedron 2002, 58, 4801.
13. Ranu, B.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270.
14. Yadav, J. S.; Reddy, B. V. S.; Srinivas, R.; Venugopal, C.; Ramalingam, T. Synthesis 2001, 1341.
15. (a) Lu, J.; Ma, H. Synlett 2000, 63.
16. (b) Lu, J.; Bai, Y. Synthesis 2002, 466.
17. Jin, T.; Zhang, S.; Li, T. Synth. Commun. 2002, 32, 1847.
18. Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 41, 9075.
19. Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 67.
20. Hu, E. H.; Slider, D. R.; Dolling, U.-H. J. Org. Chem. 1998, 63, 3454.
21. Kappe, C. O.; Kumar, D.; Varma, R. S. Synthesis 1999, 1799.
22. Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington, DC, 1990.
23. Karimi, B.; Ebrahimian, G. R.; Seradj, H. Org. Lett. 1999, 1 1737.
24. Karimi, B.; Seradj, H.; Ebrahimian, G. R. Synlett 2000, 623.
25. Karimi, B.; Seradj, H.; Tabaei, M. H. Synlett 2000, 1798.
26. Karimi, B.; Seradj, H.; Maleki, J. Tetrahedron 2002, 58, 4513.
27. (a) Bandgar, B. P.; Uppalla, L. S.; Sadavarte, V. S. Synlett 2001, 11.
28. (b) Kamal, A.; Chouhan, G. Synlett 2002, 474.
29. (c) Kamal, A.; Chouhan, G.; Ahmed, K. Tetrahedron Lett. 2002, 43, 6947.