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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Veröffentlicht in:Synthetic communications 2000-10, Vol.30 (20), p.3693-3701
Hauptverfasser: Bassin, Jatinder P., Frearson, Martin J., Al-Nawwar, Karim
Format: Artikel
Sprache:eng
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Zusammenfassung: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