Novel Synthesis of a 2H-1,2-Benzothiazine -1,1-Dioxide Derivative

Novel Synthesis of a 2H-1,2-Benzothiazine -1,1-Dioxide Derivative

We report a novel synthesis of 4-chloro-2-cyclohexyl-6,7-dimethoxy-2H-1,2-benzothiazine-1,1-dioxide 6 from 3,4-dimethoxychalcone 1. Chlorosulfonation of 1 followed by amination, then epoxidation under basic conditions with immediate elimination of the benzoyl group and electrophilic chlorination res...

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Bibliographic Details
Published in:Synthetic communications Vol. 30; no. 20; pp. 3693 - 3701
Main Authors: Bassin, Jatinder P., Frearson, Martin J., Al-Nawwar, Karim
Format: Journal Article
Language:English
Published: Taylor & Francis Group 01-10-2000
Online Access:Get full text
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Summary:We report a novel synthesis of 4-chloro-2-cyclohexyl-6,7-dimethoxy-2H-1,2-benzothiazine-1,1-dioxide 6 from 3,4-dimethoxychalcone 1. Chlorosulfonation of 1 followed by amination, then epoxidation under basic conditions with immediate elimination of the benzoyl group and electrophilic chlorination resulted in 6. A mechanism is suggested.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910008086996