A facile synthesis and thio-Claisen rearrangement of 3-aryl-2-phenyl-5- prop-2-ynylsulfanyl-3H-pyrimidin-4-ones: Regioselective transformation to thieno[3,2-d]pyrimidin-4-ones

Tetrahedron Letters

Volumn 45, Issue 31, 2004, Pages 6075-6077

  Mohan, Chander ^a   Kumar, Vipan ^a   Mahajan, Mohinder P ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CLAISEN REARRANGEMENT; DRUG SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 3142784321     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.121     Document Type: Article

References (26)

1. Lunt E. Barton D.H.R., Ollis W.D. Comprehensive Organic Chemistry. Vol. 4:1974;493 Pergamon, Oxford
2. Brown J.D. Katritzky A.R., Rees C.W. Comprehensive Heterocyclic Chemistry. Vol. 3:1984;57 Pergamon, Oxford
3. Sasaki T., Minamoto K., Suzuki T., Yamashita S. Tetrahedron. 36:1980;865
4. Bradshaw T.K., Hutchison D.W. Chem. Soc. Rev. 6:1977;43
5. Maumato R., Farukawa Y. Chem. Pharm. Bull. 25:1977;2974
6. Cheng C.C., Roth B. Progr. Med. Chem. 8:1971;61
7. Jones A.S., Swgers J.R., Walker R.T., Clercq E.D. J. Med. Chem. 31:1988;268
8. Griengl H.H., Wanck E., Schwarz W., Streicher W., Rosenwirth B., Clercq E.D. J. Med. Chem. 30:1987;1199
9. Clercq E.D., Benaerts R. J. Biol. Chem. 262:1987;14905
10. Heidelberger C. Holland J.F., Frei E. Pyrimidine and Pyrimidine Antimetabolites in Cancer Medicine. 1984;801 Lea Febiger, Philadelphia
11. Clercq E.D., Descamps J., Somer P.D., Barr P.J., Jones A.S., Walker R.T. Proc. Natl. Acad. Sci. U.S.A. 76:1979;2974
12. Heidelberger C., King D.H. Shugar D. Antiviral Agents in Pharmacology and Therapeutics. 6:1979;427 Pergamon, Oxford
13. Mitsuya H., Weinhold K.J., Furman P.A., Clair M.H., Lehraman S.N., Gallo C., Bolognesi D., Barry D.W., Boder S. Proc. Natl. Acad. Sci. U.S.A. 82:1985;7096
14. Fischl M.A., Richman D.D., Grieco M.H., Gottlieb M.S., Volberdin P.A., Laskin O.L., Leedom J.M., Groopman J.E., Mildvan D., Schooley R.T., Jackson G.G., Durack D.T., King D.N. Eng. J. Med. 317:1987;185
15. Griengl H., Bodenteich M., Hayden W., Wanek E., Steicher W., Stutz P., Bachmayer H., Ghazzouli I., Rosenwirth B. J. Med. Chem. 28:1985;1679
16. Botta M., Occhionero F., Nicoletti R., Mastromarino P., Conti C., Margini M. Saladino. Bioorg. Med. Chem. 7:1999;1925
17. Boyd H.F., Fell S.C.M., Hickey D.M.B., Ife R.J., Leach C.A., Macphee C.H., Milliner K.J., Pinto I.L., Rawlings D.A., Smith S.A., Stansfield I.G., Stanway S.J., Theobald C.J., Whittaker C.M. Bioorg. Med. Chem. Lett. 12:2002;51
18. Kawahara N., Nakajima T., Itoh T., Ogura H. Chem. Pharm. Bull. 33:1985;4740
19. Majumdar K.C., Das U. J. Chem. Res. (S). 1997;309
20. Majumdar K.C., Das U. Synth. Commun. 27:1997;4013
21. Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471
22. Sharma A.K., Jayakumar S., Hundal M.S., Mahajan M.P. J. Chem. Soc., Perkin. Trans. 1. 2002;774-784. and references cited therein
23. 2S: C, 68.94%; H, 4.63%; N, 8.04%. Found: C, 68.72%; H, 4.70%; N, 8.20%
24. 2S: C, 68.94%; H, 4.63%; N, 8.04%. Found: C, 68.73%; H, 4.73%; N, 8.19%
25. Majumdar K.C., Ghosh M., Jana M., Saha D. Tetrahedron Lett. 43:2002;2111
26. Majumdar K.C., Ghosh S.K. Tetrahedron Lett. 43:2002;2115