Phosphotungstic acid catalysed one-pot synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2-ones

Journal of Chemical Research

Volumn , Issue 3, 2004, Pages 190-191

  Jin, Tong Shou ^a   Xiao, Jin Chong ^a   Chen, Van Xue ^a   Li, Tong Shuang ^a  

^a HEBEI UNIVERSITY   (China)

Author keywords

Biginelli reaction; Dihydropyrimidinones; Phosphotungstic acid; Synthesis

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2 ONE DERIVATIVE; DIHYDROPYRIMIDINONE; PHOSPHOTUNGSTIC ACID; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 2942532319     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/0308234041640799     Document Type: Article

References (33)

1. C.O. Kappe, Tetrahedron, 1993, 49, 6937.
2. (a) K.S. Atwal, G.C. Rovnyak, S.D. Kimball, D.M. Floyd, S. Moreland, B.N. Swanson, J.Z. Gougoutas, J. Schwartz, K.M. Smillie and M.F. Malley, J. Med. Chem., 1990, 33, 2629;
3. (b) K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg and B.C. Reilly, J. Med. Chem., 1991, 38, 806;
4. (c) G.C. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, J.D. Dimarco, J.Z. Gougoutas, A. Hedberg, M.F. Malley, J.P. Carthy, R. Zhang and S. Moreland, J. Med. Chem., 1995, 38, 119;
5. (d) G.J. Grover, S. Dzwonczyk, D.M. McMullen, C.S. Normadinam, P.G. Sleph and S.J. Moreland, J. Cardiovasc. Pharmacol, 1995, 26, 289.
6. L.E. Overman, M.H. Rabinowitz and P.A. Renhowe, J. Am. Chem. Soc., 1995, 117, 2657.
7. A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C. DeBrosse, S. Mai, A. Truneh and D.J. Faulkner, J. Org. Chem., 1995, 60, 1182.
8. (a) P. Biginelli, Gazz, Chim. Ital., 1893, 23, 360;
9. (b) K.S. Atwal, G.C. Rovnyak, B.C. Reilly and J. Schwartz, J. Org. Chem., 1989, 54, 5898;
10. (c) J. Barluenga, M. Tomas, A. Ballesteros and L.A. Lopez, Tetrahedron Lett., 1989, 30, 4573.
11. (a) B.C. O'Reilly and K.S. Atwal, Heterocycles, 1987, 26, 1185;
12. (b) K.S. Atwal, B.C. O'Reilly, J.Z. Gougoutas and M.F. Malley, Heterocycles, 1987, 26, 1189;
13. (c) A.D. Shutalev, E.A. Kishko, N. Sivova and A.Y. Kuznetsov, Molecules, 1998, 3, 100.
14. (a) E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 1998, 63, 3454;
15. (b) C.O. Kappe and S.F. Falsone, Synlett, 1998, 718.
16. F. Bigi, S. Carloni, B. Frullanti, R. Maggi and G. Sartori, Tetrahedron lett., 1999, 40, 3465.
17. J. Lu and H. Ma, Synlett, 2000, 63.
18. J.S. Yadav, R.B.V. Subba, R.E. Jagan and T. Ramalingam, J. Chem. Res., 2000, 354.
19. (a) A. Studer, S. Hadida, R. Territto, S.Y. Kim, P. Jeger, P. Wipf and D.P. Curran, Science, 1997, 275, 823;
20. (b) A. Studer, P. Jeger and D.P. Curran, J. Org. Chem., 1997, 62, 2917.
21. J.S. Yadav, B.V.S. Reddy, R. Srinivas, C. Venugopal and T. Ramalingam, Synthesis, 2001, 1341.
22. K.A. Kumar, M. Kasthuraiah, C.S. Reddy and C.D. Reddy, Tetrahedron Lett., 2001, 42, 7873.
23. J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 2000, 41, 9075.
24. B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 2000, 65, 6270.
25. T.S. Jin, S.L. Zhang and T.S. Li, Synth. Commun., 2002, 32, 1847.
26. (a) I.V. Kozhevnikov, S.M. Kulikov and N.G. Chukaeve, React Kinet, Catal. Lett., 1992, 47, 59;
27. (b) T.S. Jin, Y.W. Li, G. Sun and T.S. Li, J. Chem. Res., 2002, 456.
28. (a) K. Folkers, H.J. Harwood and T.B. Johnson, J. Am. Chem. Soc., 1932, 54, 3751;
29. (b) K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 1933, 55, 3361;
30. (c) K. Singh, J. Singh, P.K. Deb and H. Singh, Tetrahedron, 1999, 55, 12873;
31. (d) J.V. Eynde, N. Audiart, V. Canonne, S. Michel, Y.V. Haverbeke and C.O. Kappe, Heterocycles, 1997, 45, 1967.
32. D.S. Rose, L. Fatima and H.B. Meteyala, J. Org. Chem., 2003, 68, 587.
33. C.O. Kappe, J. Org. Chem., 1997, 62, 7201.