A New Biginelli Reaction Procedure Using Potassium Hydrogen Sulfate as the Promoter for an Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-one

Synlett

Volumn , Issue 3, 2004, Pages 537-539

  Tu, Shujiang ^a   Fang, Fang ^a   Zhu, Songlei ^a   Li, Tuanjie ^a   Zhang, Xiaojing ^a   Zhuang, Qiya ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

Biginelli reaction; Cyclic 1,3 dicarbonyl compounds; Dihydropyrimidin 2(1H) one; Potassium hydrogen sulfate

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2(1H) ONE; GLYCOL; POTASSIUM DERIVATIVE; POTASSIUM HYDROGEN SULFATE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; BIGINELLI REACTION; CATALYSIS; DEHYDRATION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 1442360067     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815419     Document Type: Article

References (27)

1. (a) Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem. 1991, 34, 806.
2. (b) Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwart, J.; Malley, M. F. J. Med. Chem. 1992, 35, 3254.
3. (c) Grover, G. J.; Dzwonczyk, S.; Mcmullen, D. M.; Normadinam, C. S.; Slenph, P. G.; Moreland, S. J. J. Cardiovasc. Pharmacol. 1995, 26, 289.
4. Snider, B. B.; Shi, Z. P. J. Org. Chem. 1993, 58, 3828; and references cited therein.
5. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
6. O'Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185.
7. Atwal, K. S.; O'Reilly, B. C.; Gougoutas, J. Z.; Malley, M. F. Heterocycles 1987, 26, 1189.
8. Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898.
9. Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Ind. J. Chem., Sect. B 1995, 34, 151.
10. Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819.
11. Studer, A.; Hadida, S.; Ferrito, R.; Kim, S. Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
12. Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
13. Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1999, 40, 3465.
14. Hu, E. H.; Silder, D. R.; Dolling, U. H. J. Org. Chem. 1998, 63, 3454.
15. Kappe, C. O.; Kumar, D.; Varma, R. S. Synthesis 1999, 1799.
16. Lu, J.; Bai, Y. J.; Wang, Z. J.; Yang, B. Q.; Ma, H. R. Tetrahedron Lett. 2000, 41, 9075.
17. Ma, Y.; Qian, C. T.; Wang, L. M.; Yang, M. J. Org. Chem. 2000, 65, 3864.
18. Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270.
19. Ramalinga, K.; Vijayalakshmi, P.; Kaimal, T. N. B. Synlett 2001, 863.
20. Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Bubu, R.; Reddy, V. V. N. Tetrahedron Lett. 2002, 43, 2657.
21. Maiti, G.; Kundu, P.; Guin, C. Tetrahedron Lett. 2003, 44, 2757.
22. Lu, J.; Bai, Y. J. Synthesis 2002, 466.
23. Fu, N. Y.; Yuan, Y. F.; Gao, Z.; Wang, S. W.; Wang, J. T.; Peppe, C. Tetrahedron Lett. 2002, 58, 4801.
24. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Fard, M. A. Tetrahedron Lett. 2003, 44, 2889.
25. Tu, S. J.; Fang, F.; Miao, C. B.; Jiang, H.; Shi, D. Q.; Wang, X. S. Tetrahedron Lett. 2003, 44, 6153.
26. (a) Folkers, K.; Harwood, H. J.; Johnson, T. B. J. Am. Chem. Soc. 1932, 54, 3751.
27. (b) Folkers, K.; Johnson, T. B. J. Am. Chem. Soc. 1933, 55, 3784.