Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone

Journal of Heterocyclic Chemistry

Volumn 45, Issue 2, 2008, Pages 607-610

  Burbuliene, Milda M ^a   Mazeikaite, Rita ^a   Vainilavicius, Povilas ^a  

^a VILNIUS UNIVERSITY   (Lithuania)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 METHYLTHIO 4 QUINAZOLINYLOXY) 1 PHENYLETHANONE; 2 METHYLTHIO 3 (2 OXO 2 PHENYLETHYL) 4(3H)QUINAZOLINONE; 2 METHYLTHIO 3 (2 OXOPROPYL) 4(3H)QUINAZOLINONE; 2 METHYLTHIO 4(3H)QUINAZOLINONE; ACETONE; ACETONITRILE; ACETOPHENONE DERIVATIVE; BROMOACETIC ACID; BROMOACETIC ACID ETHYL ESTER; CHLOROACETONE; ETHYL (2 METHYLTHIO 4 OXO 3 QUINAZOLINYL)ACETATE; ETHYL (2 METHYLTHIO 4 QUINAZOLINYLOXY)ACETATE; METHANOL; METHOXIDE SODIUM; N,N DIMETHYLFORMAMIDE; OXIDE; PHENACYL BROMIDE; POTASSIUM CARBONATE; QUINAZOLINONE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; SUBSTITUTION REACTION;

EID: 40949119051     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450250     Document Type: Article

References (34)

1. Michael, J. P. Natural Prod. Reports 2007, 24, 223.
2. Mashe, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787.
3. Sinha, S.; Srivastava, M. Progress. Drug Res. 1994, 43, 143.
4. Horton, D. A.; Boume, G. T.; Smythe, M. C. Chem. Rev., 2003, 103, 893.
5. Baker, B. R.; Querry, M. V.; Kadish, A. F.; Williams, J. H. J. Org. Chem. 1952, 17, 35.
6. Ooi, H.; Urushibara, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2001, 3, 953.
7. Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833.
8. Takaya, Y.; Tasaka, H.; Chiba, T.; Uwai, K.; Tanitsu, H.-S.; Kim, Y.; Wataya, Y.; Miura, M.; Takeshita, M.; Oshima, Y. J. Med. Chem. 1999, 42, 3163.
9. Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175.
10. Chao, Q.; Deng, L.; Shih, H.; Leoni, L. M.; Genini, D.; Carson, D. A.; Cottan, H. B. J. Med. Chem. 1999, 42, 3860.
11. Goto; S.; Tsuboi, H.; Kanoda, M.; Mukai, K.; Kagara, K. Org. Procc. Res.& Develop. 2003, 7, 700.
12. Walter, H.; Zeun, R. Chimia 2003, 57, 692.
13. Lamberth, C. Heterocycles 2006, 68, 561.
14. Lempert, K.; Doleschall, G. Acta Chim. Acad. Sci. Hung., 1963, 37, 457;
15. Chem. Abstr. 1963, 59, 12809e.
16. Kienzle, F.; Kaiser, A.; Minder, R. E. Helv. Chim. Acta 1983, 66, 148.
17. Chan, Ch. H.; Shish, F. J.; Liu, K., Ch.; Chern, J. W. Heterocycles 1987, 26, 3193.
18. Sinha, S. K. P.; Kumar, P. Indian J. Chem. Sec. B. 1989, 28B (3), 274;
19. Chem. Abstr. 1989, 111, 174058a.
20. Malamas, M. S.; Millen, J. J. Med. Chem. 1991, 34, 1492.
21. Sauter, F.; Froehlich, J.; Blasl, K.; Gewald, K. Heterocycles 1995, 40, 851.
22. Wippich, P.; Gutschow, M.; Leistner, S. Synthesis 2000, 5, 714.
23. Gutchow, M.; Powers, J. C. J. Heterocycl. Chem. 2001, 38, 419.
24. Apfel, Ch.; Banner, D. W.; Bur, D.; Dietz, M.; Hubschwerlen, Ch.; Locher, H.; Marlin, F.; Masciardi, R.; Pirson, W.; Stadler, H. J. Med. Chem. 2001, 44, 1847.
25. Liu, J.-F.; Lee, J.; Dalton, A. M.; Bi, G.; Yu, L.; Baldino, C. M.; McElory, E.; Brown, M. Tetrahedron Lett. 2005, 46, 1241.
26. Fisnerova, L.; Brunova, B.; Maturova, E.; Grimova, J. EP 367 944, 1990; Chem. Abstr., 1991, 114, 62107w.
27. Hori, M.; Ohtaka, H. Chem. Pharm. Bull. 1993, 41, 1114;
28. Chem. Abstr. 1994, 120, 217509d.
29. Kovalenko, S. I.; Siniak, R. S.; Mazur, I. A.; Belenichev, I. F.; Stebliuk, P. N. Farm. Zh. (Kiev) 1992, 5-6, 38 (Russ.);
30. Chem. Abstr. 1993, 119, 8762w.
31. Chen, G. S.; Kalchar, S.; Kuo, Ch.-W.; Chang, Ch.-S.; Usifoh, C. O.; Chern, J.-W. J. Org. Chem. 2003, 68, 2502.
32. Burbuliene, M. M.; Bobrovas, O.; Vainilavicius, P. J. Heterocycl. Chem. 2006, 43, 43.
33. Shevalev, S. A. Russ. Chem. Rev. 1970, 39, 844.
34. Orysyk, V. V.; Zborovskij, Yu. L.; Staninets, V. I.; Dobosh, A. A.; Khripak, S. M. Chem. Heterocycl. Comp. 2003, 39, 640.