A study of the synthesis and some reactions of 3-phenyl-1,4-benzothiazines |
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Authors: | Max Wilhelm Paul Schmidt |
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Abstract: | Condensation of o-aminothiophenol with 2-bromoacetophenone yields 3-phenyI-1,4-benzo-thiazine hydrobromide, which upon treatment with alkali gave a mixture of 3-phenyl-2H-1,4-benzothiazine (VIIa) and 3-phenyl-4H-1,4-benzothiazine (VIIb). Catalytic hydrogenation led to rearrangement of the benzothiazine (VIIa) to 2-phenyl-2-methyl-2,3-dihydrobenzothiazole (X), while reduction with lithium aluminium hydride resulted in 3-phenyl-2,3-dihydro-4H-1,4-benzothiazine (XVI). The latter was transferred to 3-phenyl-4-aminoalkyl-2,3-dihydro-4H-1,4-benzothiazines (XVII and XVIII). |
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