Heterocyclic bioantioxidants 1. Reaction of 3-nitro-4-chlorocoumarin with thiolating agents
Tóm tắt
The reaction of 3-nitro-4-chlorocoumarin with thiolating agents in the presence of water leads to the formation of a mixture of 3-nitro-4-hydroxycoumarin, bis(3-nitro-4-coumarinyl) sulfide, and colored labile products of undetermined structure. The reaction path can be controlled by the choice of solvent, reagent ratio, and temperature regime and by the use of weakly basic additives.
Tài liệu tham khảo
é. A. Parfenov, V. L. Savel'ev, and L. D. Smirnov, Fifth Moscow Conference on Organic Chemistry and Technology. Abstracts [in Russian], Moscow (1989), p. 209.
E. B. Burlakova and N. G. Khrapova, Usp. Khim., 54, 1540 (1985).
é. A. Parfenov and L. D. Smirnov, Khim.-Farm. Zh., 22, 1438 (1988).
F. Bergel, A. Jacob, A. R. Todd, and T. S. Wock, J. Chem. Soc., 1375 (1938).
J. D. Hepworth, T. K. Jones, and R. Livingstone, Tetrahedron, 37, 2613 (1981).
B. M. Howard, K. Clarkson, and R. L. Bernstein, Tetrahedron Lett., No. 46, 4449 (1979).
W. S. Bowers, U. S. Patent No. 4656189; Chem. Abs., 107, 115493 (1987).
R. D. H. Murray, J. Mendez, and S. A. Brown, The Natural Coumarins. Occurrence, Chemistry, and Biochemistry, Wiley, Chichester (1982), p. 271.
D. T. Witiak, S. K. Kim, K. Romstedt, H. A. I. Newman, and D. R. Feller, J. Med. Chem., 29, 2170 (1986).
K. Shinohara, Y. K. Tseng, Y. Tomita, U. Inoue, T. Sonoda, H. Murakami, and H. Omura, Kyushu Daigaku Nogakubu Gakugei Zasshi, 34, 59 (1980); Chem. Abs., 93, 37080 (1980).
V. L. Savel'ev, O. S. Artamonova, V. S. Troitskaya, V. G. Vinokurov, and V. A. Zagorevskii, Khim. Geterotsikl. Soedin., No. 7, 885 (1973).
M. G. Nair, L. H. Boyce, and M. A. Berry, J. Org. Chem., 46, 3351 (1981).
J. Staunton, Comprehensive Organic Chemistry (editors D. Barton and J. Ollis) [Russian translation], Vol. 9, Khimiya, Moscow (1985), p. 61.
V. D. Shner, N. N. Artamonova, T. I. Petrukhina, V. F. Seregina, and B. V. Salov, Zh. Org. Khim., 25, 879 (1989).
L. V. Timokhina, V. A. Usov, L. I. Lavlinskaya, and M. G. Voronkov, Zh. Org. Khim., 21, 119 (1985).
B. B. Kumar, V. J. T. Raju, V. Ranabaore, and M. C. Ganorkar, Nat. Acad. Sci. Lett., 8, 233 (1985).
C. Willgerodt, Berichte, 17, Ref., 353 (1884).
G. P. Sharnin, V. V. Nurgatin, and B. I. Buzykin, Zh. Org. Khim., 3, 1245 (1967).