82409-32-3Relevant articles and documents
SYNTHESIS AND REACTIONS OF HALO DERIVATIVES OF 4-ISOPROPYL-2H-1,4-THIAZIN-3-ONE
Masuda, Ryoichi,Hojo, Masaru,Ichi, Tadaaki,Adachi, Fujio,Yoshinaga, Kenji
, p. 143 - 152 (2007/10/02)
Reaction of 4-isopropyl-2H-1,4-thiazin-3-one 1 (R=i-Pr) with N-chloro- and N-bromosuccinimide occurred exclusively at the 6-position to give 6-chloro and 6-bromo derivatives of 1 (R=i-Pr), respectively, in high yield, in sharp contrast to the 2-aroyloxylation by benzoyl peroxide or m-chloroperbenzoic acid reported earlier.Reaction of 1 (R=i-Pr) with methanesulfonyl chloride in the presence of aluminum chloride afforded an addition compound, 4-isopropyl-5,6-dichloro-1,4-tetrahydrothiazin-3-one.The 2-chloro derivative 6 of 1 (R=i-Pr) was successfully prepared by hydrolysis of the 2-m-chlorobenzoyloxy derivative of 1 (R=i-Pr) followed by treatment with thionyl chloride.Derivative 6 reacted readily under mild conditions with water, alcohols, thiols, ammonia and amines to give various 2-substituted compounds of 1 (R=i-Pr).With phenol as a nucleophile, 1 (R=i-Pr) reacted exclusively at the para position.Reaction at carbon atoms also occurred with N,N-dimethylaniline and 2,6-xylidine.
