Selective Synthesis of 1,2-Benzisothiazol-3-one-1-Oxide Nitro Derivatives

Abstract

A new selective synthesis of 1,2-benzisothiazol-3-one-1-oxide nitro derivatives by reaction of 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in wet CH₂Cl₂ has been developed. Reactions of N-unsubstituted 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in 60% AcOH give, instead of the S-oxides, the appropriate 1,2-benzisothiazol-3-one-1,1-dioxide nitro derivatives.

Key words

polynitrobenzamides - chlorine - 1,2-benzisothiazole-3-one-1-oxides - 1,2-benzisothiazole-3-one-1,1-dioxides

References

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  Samet, A. V.; Zakharov, E. P.; Semenov, V. V.; Buchanan III, A. C.; Gakh, A. A. Synth. Commun. 2001, in press.