Syntheses of sulfoxide derivatives in the benzodiazine series. Diazines. Part 37

Tetrahedron

Volumn 60, Issue 36, 2004, Pages 7983-7994

  Le Fur, Nicolas ^a   Mojovic, Ljubica ^a   Turck, Alain ^a   Plé, Nelly ^a   Quéguiner, Guy ^a   Reboul, Vincent ^b   Perrio, Stéphane ^b   Metzner, Patrick ^b  

^a IRCOF   (France)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

Benzodiazines; Cinnolines; Phtalazines; Quinazolines; Quinoxaline; Sulfoxides

Indexed keywords

2 (4 TOLYL)SULFANYLQUINOXALINE; 2 (4 TOLYL)SULFINYLQUINOXALINE; 2 PHENYL 4 TERT BUTYLSULFANYLQUINAZOLINE; 2 TERT BUTYL 5 TERT BUTYLSULFINYL 4(3H) QUINAZOLINONE; 2 TERT BUTYL 8 TERT BUTYLSULFINYL 4(3H) QUINAZOLINONE; 2 TERT BUTYLSULFANYLQUINOXALINE; 2 TERT BUTYLSULFINYLQUINOXALINE; 3 (4 TOLYL)SULFANYLCINNOLINE; 3 (4 TOLYL)SULFINYLCINNOLINE; 3 METHOXY 4 PHENYLSULFANYLCINNOLINE; 3 METHOXY 4 PHENYLSULFINYLCINNOLINE; 3 TERT BUTYL 4 TERT BUTYLSULFANYLCINNOLINE; 3 TERT BUTYL 4 TERT BUTYLSULFINYLCINNOLINE; 3 TERT BUTYLCINNOLIN 4 OL; 3 TERT BUTYLSULFANYLCINNOLINE; 3 TERT BUTYLSULFINYLCINNOLINE; 4 CHLORO 3 TERT BUTYLCINNOLINE; 4 METHYLSULFANYLCINNOLINE; 4 PHENYLSULFANYLCINNOLINE; 4 PHENYLSULFINYLCINNOLINE; 4 TERT BUTYLSULFANYLCINNOLINE; 4 TERT BUTYLSULFINYLCINNOLINE; 4 TERT BUTYLSULFONYLCINNOLINE; 6,7 DIMETHOXY 4 (4 TOLYL)SULFANYLCINNOLINE; 6,7 DIMETHOXY 4 (4 TOLYL)SULFINYLCINNOLINE; 6,7 DIMETHOXY 4 TERT BUTYLSULFANYLCINNOLINE; 6,7 DIMETHOXY 4 TERT BUTYLSULFINYLCINNOLINE; QUINAZOLINE DERIVATIVE; QUINOXALINE DERIVATIVE; SULFADIAZINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 4043180599     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.059     Document Type: Article

References (48)

1. Brown D.J. The Chemistry of Heterocyclic Compounds. 1996;Wiley, New York
2. Heinisch H., Frank H. Ellis G.P., West G.G. Progress in Medicinal Chemistry. 1990;Elsevier, Amsterdam
3. Rewcastle G.W., Denny W.A., Bridges A.J., Zhou H., Cody D.R., McMichael A., Fry D.W. J. Med. Chem. 38:1995;3482-3487
4. Gazit A., App H., McMahon G., Chen J., Levitzki A., Bohmer F.D. J. Med. Chem. 39:1996;2170-2177
5. Curd F.H.S., Landquist J.K., Rose F.L. J. Chem. Soc. 1947;775-783
6. Rastogi V.K., Parmar S.S., Singh S.P., Akers T.K. J. Heterocyclic Chem. 15:1978;497-499
7. Wolfe J.F., Rathman T.L., Sleevi M.C., Campbell J.A., Greenwood T.D. J. Med. Chem. 33:1990;161-166
8. Hori M., Iemura R., Hara H., Ozaki A., Sukamoto T., Ohtaka H. Chem. Pharm. Bull. 38:1990;681-687
9. Melikian A., Schlewer G., Chambon J.P., Wermuth C.G. J. Med. Chem. 35:1992;4092-4097
10. Lee S.J., Konishi Y., Yu D.T., Miskowski T.A., Riviello C.M., Macina O.T., Frierson M.R., Kondo K., Sugitani M., Sircar J.C., Blazejewski K.M. J. Med. Chem. 38:1995;3547-3557
11. Levin, J. I.; Venkatesan, A. M. U.S. Patent 5,284,853-A, 1994.
12. Kurogi Y., Inoue Y., Tsutsumi K., Nakamura S., Nagao K., Yoshitsugu H., Tsuda Y. J. Med. Chem. 39:1996;1433-1437
13. Jiang J.B., Hesson D.P., Dusak B.A., Dexter D.L., Kang G.J., Hamel E. J. Med. Chem. 33:1990;1721-1728
14. Sehlstedt U., Aich P., Bergman J., Vallberg H., Norden B., Graslund A. J. Mol. Biol. 278:1998;31-56
15. Newkome G.R., Paudler W.W. Contemporary Heterocyclic Chemistry: Synthesis, Reactions and Applications. 1982;Wiley, New York. pp 214-215, and references cited therein
16. Bruce J.M. J. Chem. Soc. 1959;2366-2375
17. Besford L.S., Bruce J.M. J. Chem. Soc. 1964;4037-4044
18. Eicher T., Hauptmann S. The Chemistry of Heterocycles. 1995;Thieme, New York
19. Juncai F., Yang L., Quinghua M., Bin L. Synth. Commun. 28:1998;193-196
20. Barluenga J., Aznar F., Liz R., Cabal M.-P. Synthesis. 1985;313-314
21. Petukhov P.A., Tkachev A.V. Tetrahedron. 53:1997;9761-9768
22. Curd F.H.S., Landquist J.K., Rose F.L. J. Chem. Soc. 1948;1759
23. Clark-Lewis J.W., Singh R.P. J. Chem. Soc. 1962;3162
24. Armarego W.L.F. J. Chem. Soc. 1961;2697
25. Sen A.B., Gupta S.K. J. Indian Chem. Soc. 32:1962;368
26. Downes A.M., Lions F. J. Am. Chem. Soc. 72:1950;3053
27. Katritzky A.R., Pozharski A.F. Handbook of Heterocyclic Chemistry. 2nd ed.:2000;Pergamon, New York
28. See for example: Wada A., Yamamoto K., Ohki K., Nagai S., Kanamoto S. J. Heterocyclic Chem. 29:1992;911
29. Turck A., Plé N., Pollet P., Mojovic L., Duflos J., Quéguiner G. J. Heterocyclic Chem. 34:1997;621-627
30. Turck A., Plé N., Pollet P., Quéguiner G. J. Heterocyclic Chem. 35:1998;429-436
31. Pollet P., Turck A., Plé N., Quéguiner G. J. Org. Chem. 64:1999;4512-4515
32. Gautheron Chapoulaud V., Plé N., Turck A., Quéguiner G. Tetrahedron. 56:2000;5499-5507
33. Turck A., Plé N., Tallon V., Quéguiner G. Tetrahedron. 51:1995;13045-13060
34. Tallon, V., PhD Thesis, University of Rouen, France, 1996.
35. Castle R.N., Kruse F.H. J. Org. Chem. 17:1952;1571-1575
36. Simpson J.C.E. J. Chem. Soc. 1946;94-97
37. Phillips S.D., Castle R.N. J. Heterocyclic Chem. 17:1980;1489-1495
38. Alford E.J., Schofield K. J. Chem. Soc. 1952;2102
39. Alford E.J., Schofield K. J. Chem. Soc. 1953;609
40. Alford E.J., Schofield K. J. Chem. Soc. 1953;1811
41. Druey J., Ringier B.H. Helv. Chim. Acta. 34:1951;195-205
42. Barlin G.B., Brown W.V. J. Chem. Soc. (B). 1968;1435-1445
43. Sandrinelli F., Perrio S., Beslin P. J. Org. Chem. 62:1997;8626-8627
44. Sandrinelli F., Perrio S., Averbuch-Pouchot M.-T. Org. Lett. 4:2002;3619-3622
45. Audoux, J., PhD Thesis, University of Rouen, France, 2002.
46. Gelling I.R., Wibberley D.G. J. Chem. Soc. (C). 1969;931-934
47. Castle R.N., Ward H., White N., Adachi K. J. Org. Chem. 25:1960;570-572
48. Barlin G.B., Brown W.V. J. Chem. Soc. (B). 1969;333-336