Expeditious routes to 4-alkoxyquinazoline-2-carbonitriles and thiocarbamates via N-arylimino-1,2,3-dithiazoles using microwave irradiation

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6475-6484

  Besson, Thierry ^a   Dozias, Marie Joëlle ^b   Guillard, Jérôme ^a   Jacquault, Patrick ^b   Legoy, Marie Dominique ^a   Rees, Charles W ^c  

^a UNIVERSITÉ DE LA ROCHELLE   (France)

^b Prolabo Groupe Merck   (France)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 ALKOXYQUINAZOLINE 2 CARBONITRILE; ISOTHIOCYANIC ACID; N ARYLIMINO 1,2,3 DITHIAZOLE DERIVATIVE; PYRROLE DERIVATIVE; QUINAZOLINE DERIVATIVE; THIOCARBAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032482292     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00276-2     Document Type: Article

References (26)

1. 3. a) Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279.
2. b) Giguere, R.; J. Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945.
3. 4. For reviews see: a) Caddick, S. Tetrahedron 1995, 51, 10403;
4. b) Bougrin, K.; Soufiaoui, M.; Loupy, A.; Jacquault, P. New J. Chem. 1995, 19, 213, and references cited therein;
5. c) Galema, S. A. Chem. Soc. Rev. 1997, 26, 233.
6. 5. a) Besson, T.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1996, 2857.
7. b) Bénéteau, V.; Besson, T.; Rees, C. W. Synth. Commun., 1997, 27, 2275.
8. 6. Appel, R.; Janssen, H.; Siray, M.; Knoch, F. Chem. Ber. 1985, 118, 1632. The salt 1 is a pale greenish yellow solid, insoluble in organic solvents. It is completely stable in a dry inert atmosphere but reacts slowly with moisture to form 4-chloro-1,2,3-dithiazol-5-one.
9. 7. Rees, C. W. J. Heterocycl. Chem. 1992, 29, 639.
10. 8. English, R. F.; Rakitin, O. A.; Rees, C. W.; Vlasova, O. G. J. Chem. Soc., Perkin Trans. 1 1997, 201
11. 9. Besson, T.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1, 1995, 1659.
12. 10. Rakitin, O. A.; Rees, C. W.; Vlasova, O. G. Tetrahedron Lett. 1996, 37, 4589.
13. 11. a) Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1995, 1419;
14. b) Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1995, 2097.
15. 12. Besson, T.; Guillaumet, G.; Lamazzi, C.; Rees, C. W. Synlett 1997, 704.
16. 13. a) Krantz, A.; Spencer, R. W.; Tam, T. F.; Liak, T. J.; Copp, L. J.; Thomas, E. M.; Rafferty, S. P. J. Med. Chem. 1990, 29, 1349;
17. b) Jarvest, L. R.; Parratt, M. J.; Debouck, C. M.; Gorniak, J. G.; Jennings, L. J.; Serafinowska, H. T.; Strickler, J. E. Bioorg. Med. Chem. Lett. 1996, 6, 2463;
18. c) Gilmore, J. L.; Hays, S. J.; Caprathe, B. W.; Lee, C.; Emmerling, M. R.; Michael, W.; Jaen, J. C. Bioorg. Med. Chem. Lett. 1996, 6, 679;
19. d) Takase, Y.; Saeki, T.; Watanabe, N.; Adachi, H.; Souda, S.; Saito, I. J. Med. Chem. 1994, 37, 2106.
20. 14; Guillard, J. unpublished results.
21. 15. a) Commarmot, R.; Diderot, R.; Gardais, J. F. Rhône-Poulenc/Prolabo, patent 84/03496, 02 March, 1984.
22. b) Jacquault, P. Prolabo, Fr. Pat. FR 9116286, 23 December, 1991.
23. 16. a) Besson, T.; Guillard, J.; Rees C. W.; Thérisod, M. Chem. Commun., 1997, 881;
24. b) Besson, T.; Guillard, J.; Rees, C. W.; Thiéry, V. J. Chem. Soc., Perkin Trans. 1 1998, 889.
25. 17. Walter, W.; Bode, K. D. Angew. Chem., Int. Ed. Engl. 1967, 6, 281.
26. 18. Stevens, M. F. G.; McCall, C. J.; Lelieveld, P.; Alexander, P.; Richter, A.; Davies, D. E. J. Med. Chem. 1994, 37, 1689.