2-Trifluoromethyl-4H-thiochromen-4-one and 2-trifluoromethyl-4H- thiochromene-4-thione: Synthesis and reactivities

Russian Chemical Bulletin

Volumn 55, Issue 3, 2006, Pages 523-528

  Usachev, B I ^a   Shafeev, M A ^a   Sosnovskikh, V Ya ^a  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

2 trifluoromethyl 4H thiochromen 4 one; 2 trifluoromethyl 4H thiochromene 4 thione; anils; And oxime of thiochromone; Azine; Hydrazones; Oxidation; Reduction

Indexed keywords

EID: 33747123009     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-006-0286-z     Document Type: Article

References (38)

1. G. P. Ellis, in The Chemistry of Heterocyclic Compounds, Ed. G. P. Ellis, Wiley, New York, 1977, 31.
2. V. Ya. Sosnovskikh, Usp. Khim., 2003, 72, 550
3. [Russ. Chem. Rev., 2003, 72, 489 (Engl. Transl)].
4. C. Morin and R. Beugelmans, Tetrahedron, 1977, 33, 3183.
5. V. Szabó, J. Borbély, E. Theisz, and S. Nagy, Tetrahedron, 1986, 42, 4215.
6. W. Baker, J. B. Harborne, and W. D. Ollis, J. Chem. Soc., 1952, 1294.
7. W. Baker, J. B. Harborne, and W. D. Ollis, J. Chem. Soc., 1952, 1303.
8. W. Baker, G. G. Clarke, and J. B. Harborne, J. Chem. Soc., 1954, 998.
9. J. P. Huke, I. H. Hillier, R. M. Infield, and J. L. Suschitzky, J. Chem. Soc., Perkin Trans. 2, 1984, 2119.
10. B. I. Usachev, M. A. Shafeev, and V. Ya. Sosnovskikh, Izv. Akad. Nauk, Ser. Khim., 2004, 2188
11. [Russ. Chem. Bull., Int. Ed., 2004, 53, 2285 (Engl. Transl.)].
12. N. Lozaćh, L. Legrand, and N. Bignebat, Bull. Soc. Chim. Fr., 1964, 3247.
13. R. K. Razdan, R. J. Bruni, A. C. Mehta, K. K. Weinhardt, and Z. B. Papanastassiou, J. Med. Chem., 1978, 21, 643.
14. H. Nakazumi and T. Kitao, Bull. Chem. Soc. Jpn, 1980, 53, 2415.
15. H.-K. Wang, K. F. Bastow, L. M. Cosentino, and K.-H. Lee, J. Med. Chem., 1996, 39, 1975.
16. M. H. Holshouser, L. J. Loeffler, and I. H. Hall, J. Med. Chem., 1981, 24, 853.
17. T. Patonay, W. Adam, A. Lévai, P. Kövér, M. Németh, E.-M. Peters, and K. Peters, J. Org. Chem., 2001, 66, 2275.
18. H. Nakazumi, T. Ueyama, and T. Kitao, J. Heterocycl. Chem., 1984, 21, 193.
19. P. Cozzi and A. Pillan, J. Heterocycl. Chem., 1988, 25, 1613.
20. A. I. Kiprianov and A. I. Tolmachev, Zh. Obshch. Khim., 1959, 29, 2868
21. [J, Gen. Chem. USSR, 1959, 29 (Engl. Transl.)].
22. S. Y. Dike and M. Mahalingam, Synth. Commun., 1989, 19, 3443.
23. F. J. Zhang and Y. L. Li, Synthesis, 1993, 565.
24. H. Nakazumi, T. Ueyama, H. Sonoda, and T. Kitao, Bull. Chem. Soc. Jpn, 1984, 57, 2323.
25. H. Nakazumi, T. Ueyama, and T. Kitao, J. Heterocycl. Chem., 1985, 22, 1593.
26. C. H. Chen, G. A. Reynolds, H. R. Luss, and J. H. Perlstein, J. Org. Chem., 1986, 51, 3282.
27. F. Eiden and A. Engelhardt, Arch. Pharm. Ber. Deutsch. Pharm. Ges., 1967, 300, 211.
28. R. Neidlein and I. Körber, Arch. Pharm. (Weinheim, Ger.), 1978, 311, 236.
29. P. D. Clarke, A. O. Fitton, H. Suschitzky, T. W. Wallace, H. A. Dowlatshahi, and J. L. Suschitzky, Tetrahedron Lett., 1986, 27, 91.
30. V. Ya. Sosnovskikh, B. I. Usachev, D. V. Sevenard, and G.-V. Röschenthaler, J. Fluorine Chem., 2005, 126, 779.
31. K. Tamura, T. Ishihara, and H. Yamanaka, J. Fluorine Chem., 1994, 68, 25.
32. B. I. Usachev, V. Ya. Sosnovskikh, M. A. Shafeev, and G.-V. Röschenthaler, Phosphorus, Sulfur, Silicon, Relat. Elem., 2005, 180, 1315.
33. M. Topolski, J. Org. Chem., 1995, 60, 5588.
34. A. Arduini, A. Bosi, A. Pochini, and R. Ungaro, Tetrahedron, 1985, 41, 3095.
35. J. M. Khurana and S. Chauhan, J. Chem. Res. (S), 2002, 201.
36. N. S. Prostakov, V. G. Pleshakov, T. S. Seitembetov, D. A. Fesenko, and L. Olubazho Onasan'ya, Zh. Org. Khim., 1977, 13, 1484
37. [J. Org. Chem. USSR, 1977, 13 (Engl. Transl.)].
38. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209.