One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using boric acid as catalyst

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6153-6155

  Tu, Shujang ^a   Fang, Fang ^a   Miao, Chunbao ^a   Jiang, Hong ^a   Feng, Youjian ^a   Shi, Daqing ^a   Wang, Xiangshan ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALDEHYDE DERIVATIVE; BORIC ACID; PYRIMIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; REACTION TIME;

EID: 0037629580     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01466-7     Document Type: Article

References (28)

1. Biginelli P. Gazz. Chim. Ital. 23:1893;360-416.
2. Atwal K.S., Swanson B.N., Unger S.E., Floyd D.M., Moreland S., Hedberg A., O'Reilly B.C. J. Med. Chem. 34:1991;806-811.
3. 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. 35:1992;3254-3263.
4. Grover G.J., Dzwonczyk S., Mcmullen D.M., Normadinam C.S., Slenph P.G., Moreland S.J. J. Cardiovase Pharmacol. 26:1995;289-294.
5. Snider B.B., Shi Z.P. J. Org. Chem. 58:1993;3828-3839. and references cited therein.
6. O'Reilly B.C., Atwal K.S. Heterocycles. 26:1987;1185-1188.
7. Atwal K.S., O'Reilly B.C., Gougoutas J.Z., Malley M.F. Heterocycles. 26:1987;1189-1192.
8. Atwal K.S., Rovnyak G.C., O'Reilly B.C., Schwartz J. J. Org. Chem. 54:1989;5898-5907.
9. Gupta R., Gupta A.K., Paul S., Kachroo P.L. Ind. J. Chem. 34B:1995;151-152.
10. Wipf P., Cunningham A. Tetrahedron Lett. 36:1995;7819-7822.
11. Studer A., Hadida S., Ferrito R., Kim S.Y., Jeger P., Wipf P., Curran D.P. Science. 275:1997;823-826.
12. Studer A., Jeger P., Wipf P., Curran D.P. J. Org. Chem. 62:1997;2917-2924.
13. Bigi F., Carloni S., Frullanti B., Maggi R., Sartori G. Tetrahedron Lett. 40:1999;3465-3470.
14. Hu E.H., Silder D.R., Dolling U.H. J. Org. Chem. 63:1998;3454-3457.
15. Kappe C.O., Kumar D., Varma R.S. Synthesis. 1999;1799-1803.
16. Lu J., Bai Y.J., Wang Z.J., Yang B.Q., Ma H.R. Tetrahedron Lett. 41:2000;9075-9078.
17. Ma Y., Qian C.T., Wang L.M., Yang M. J. Org. Chem. 65:2000;3864-3868.
18. Xia M., Wang Y.G. Tetrahedron Lett. 43:2002;7703-7705.
19. Ranu B.C., Hajra A., Jana U. J. Org. Chem. 65:2000;6270-6272.
20. Ramalinga K., Vijayalakshmi P., Kaimal T.N.B. Synlett. 2001;863-865.
21. Lu J., Ma H.R. Synlett. 2000;63-64.
22. Lu J., Bai Y.J. Synthesis. 4:2002;466-470.
23. Tu S.J., Zhou J.F., Cai P.J., Wang H., Feng J.C. Synth. Commun. 32:2002;147-151.
24. Tu S. J., Fang F., Miao C. B., Jiang H., Shi D. Q. J. Chin. Chem. 21:2003;706-709.
25. 5. Calcd: C, 47.94; H, 3.71; N, 12.90. Found: C, 47.80; H, 3.52; N, 12.76%.
26. 2=0.1167. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 194807. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-3366-033; e-mail: deposit@ccdc.cam.ac.uk).
27. Folkers K., Harwood H.J., Johnson T.B. J. Am. Chem. Soc. 54:1932;3751-3758.
28. Folkers K., Johnson T.B. J. Am. Chem. Soc. 55:1933;3784-3791.