Chemical and Pharmaceutical Bulletin p. 1025 - 1028 (1992)
Update date:2022-07-31
Topics:
Yamazaki
Harada
Matsuzaki
Watanabe
Saito
5-Methyl-2,3-dioxo-2H,4H-1,4-thiazine (7) was obtained by the oxidation of 5-methyl-2H-1,4-thiazin-3(4H)-one (5) with m-chloroperbenzoic acid in MeOH, followed by acid hydrolysis of the resulting 2,2-dimethoxy-1,4-thiazine (6). 3-Chloro-2-oxo-1,4-thiazine (10), which was obtained from 7 by heating with phosphorous oxychloride, reacted with various nucleophiles to give 3-substituted 2-oxo-1,4-thiazines (11a-y). Some of these 2-oxo-1,4-thiazines, 11a-b, e, o and r-s, showed a protective effect against endotoxin shock in D-galactosamine-sensitized mice.
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