Synthesis of substituted uracils by the reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles under focused microwave irradiation

Tetrahedron

Volumn 61, Issue 12, 2005, Pages 3107-3113

  Fang, Woei Ping ^a   Cheng, Yuh Tsyr ^a   Cheng, Yann Ru ^a   Cherng, Yie Jia ^a  

^a CHUNGTAI INST HLTH SCI TECHNOL   (Taiwan)

Author keywords

Halouracils; Microwave irradiation; Nucleophilic substitution

Indexed keywords

1,3 DIMETHYL 5 PHENYLTHIOURACIL; 1,3 DIMETHYL 5 PIPERIDYLURACIL; 1,3 DIMETHYL 6 ETHOXYURACIL; 1,3 DIMETHYL 6 PHENOXYURACIL; 1,3 DIMETHYL 6 PHENYLTHIOURACIL; 5 (BENZYLMETHYLAMINO)URACIL; 5 ANILINOURACIL; 5 BENZYLAMINOURACIL; 5 BUTYLAMINOURACIL; 5 CYCLOHEXYLAMINOURACIL; 5 MORPHOLINOURACIL; 5 PHENYLSELENENYLURACIL; 5 PHENYLTHIOURACIL; 5 PIPERIDYLURACIL; 6 (BENZYLMETHYLAMINO)URACIL; 6 ANILINOURACIL; 6 BENZYLAMINOURACIL; 6 CYCLOHEXYLAMINOURACIL; 6 METHOXYURACIL DERIVATIVE; 6 MORPHOLINOURACIL; 6 PHENYLSELENOURACIL; 6 PHENYLTHIOURACIL; 6 PIPERIDYLURACIL; NITROGEN DERIVATIVE; OXYGEN DERIVATIVE; SELENIUM DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; URACIL; URACIL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HEATING; INTERMETHOD COMPARISON; MICROWAVE IRRADIATION; MICROWAVE RADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; SUBSTITUTION REACTION; TECHNIQUE; TIME;

EID: 14644415517     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.085     Document Type: Article

References (32)

1. B.R. Baker J. Med. Chem. 10 1967 297
2. B. Preussel, G. Etzold, D. Barwolff, and P. Langen Biochem. Pharmacol. 18 1969 2035
3. P. Langen, G. Etzold, D. Barwolff, and B. Preussel Biochem. Pharmacol. 16 1967 1833
4. B.R. Baker, and J.L. Kelley J. Med. Chem. 13 1970 461
5. R.F. Schinazi, J. Arbiser, T.I. Kalman, D. Barwolff, and B. Preussel J. Med. Chem. 29 1986 1293
6. Y.-J. Cherng Tetrahedron 56 2000 8287 8289
7. Y.-J. Cherng Tetrahedron 58 2002 887 890
8. G. Xu, and Y.-G. Wang Org. Lett. 6 2004 985
9. S. Narayan, Y. Seelhammer, and R.E. Gawley Tetrahedron Lett. 45 2004 757
10. G. Luo, L. Chen, and G.S. Poindexter Tetrahedron Lett. 43 2002 5739
11. M.F. Pilar, M. Pedro, and A.S. Miguel Synlett 2 2001 218
12. C.R. Strauss Aust. J. Chem. 52 1999 83
13. V. Sridor Curr. Sci. 74 1998 446
14. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, and D. Mathe Synthesis 1998 1213
15. H. Inoue, and T. Uead Chem. Pharm. Bull. 26 1978 2657
16. S. Senda, K. Hirota, and T. Asao J. Org. Chem. 40 1975 353
17. F.R. Gerns, and A. Perrota J. Med. Chem. 9 1966 108
18. R. Barbara, and J.F. Bunnett J. Am. Chem. Soc. 20 1965 341
19. K. Ikeda, T. Sumi, K. Yokoi, and Y. Mizuno Chem. Pharm. Bull. 13 1970 461
20. P.P. Arthur J. Am. Chem. Soc. 73 1951 1061
21. N.M. Goudgaon, N.M. Naguib, M.H. Kouni, and R.F. Schinazi J. Med. Chem. 36 1993 4250
22. B.R. Baker, and W. Rzeszotarski J. Med. Chem. 9 1967 1109
23. B.R. Baker, and W. Rzeszotarski J. Med. Chem. 11 1968 639
24. J.M. Mccall, B.V. Kamdar, and D. Kloosterman Synthesis 2 1980 123
25. Z. Ledochowski Rocz. Chem. 41 1967 215
26. S. Kumar, and S. Swapandeep Indian J. Chem. Sect. B 28 1989 1079
27. R.D. Youssefyeh, and M. Weisz Tetrahedron Lett. 1973 4317
28. K.A. Krasnov, V.I. Slesarev, and Z.L. Artem'eva J. Org. Chem. USSR 25 1989 1402
29. J. Fisher J. Am. Chem. Soc. 54 1932 727
30. G. Taylor J. Org. Chem. 30 1965 655
31. L.V. Reis, A.M. Lobo, S. Prabhakar, and M.P. Duarte Eur. J. Org. Chem. 1 2003 190
32. A. Schmidt, A. Hetzheim, and D. Albrecht Heterocycles 43 1996 2153