The Synthesis of the 1,2,4-Thiadiazine-1,1-dioxides

概要

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N-(2-Phenylethene-1-sulfonyl)-N′-monoalkyl S-methylisothioureas, 2, were ring-closed to yield Michael cycloadducts, 3-methylthio-4-alkyl-5-phenyl-1,1-dioxo-5,6-dihydro-1,2,4-thiadiazines, 3. Bulky N′-alkyl groups hindered the cycloaddition. The base-catalyzed hydrolysis of 3 and 3-chloro-derivatives 4 gave 4-methyl-5-phenyl-2,3,5,6-tetrahydro-1,1,3-trioxo-1,2,4-thiadiazines, 5, which in turn underwent N-alkylation to give 6. The reaction of 4 with amines or with sodium methoxide yielded 3-amino-, 7, or 3-methoxy-thiadiazine derivatives, 9.
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