Studies on 1,4-benzothiazines. IV. Reactions of 2-acyl-4H-1,4-benzothiazines with hydroxylamine, hydrazine, guanidine and acetamidine.

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2-Acyl-4-methyl-4H-1, 4-benzothiazines (1a, b) reacted with hydroxylamine to give dihydroisoxazolo [4, 5-b] [1, 4] benzothiazines (3a, b). However, the reaction of 1a with hydrazine did not give the dihydropyrazolo [4, 5-b] [1, 4] benzothiazine derivative corresponding to 3a, but gave its dehydro compound (6). On the other hand, in the reaction of 1b with hydrazine, formation of a pyrazole ring and opening of the thiazine ring occurred to afford a 4-(2-aminophenylthio) pyrazole derivative (7). Guanidine and acetamidine also reacted with 1a, b to give 5-[2-(N-methylamino) phenylthio] pyrimidines (10a-d).

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