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■ Facile Synthesis of 2-Substituted 4H-1,3-thiazines and 3-Substituted 1,2-Isothiazoles via Benzyne Intermediates

Ramadas Sathunuru, Hongming Zhang, Chrles W. Rees, and Edward Biehl*

*Chemistry Department, Southern Methodist University, Dallas, TX 75275-0314, U.S.A.

Abstract

Substituted 2-dialkylamino-4H-1,3-benzothiazines were Synthesizedby the reaction of (phenyl)[o-(trimethylsilyl)aryl]iodonium triflates and dialkyl-aminothiazadienes in the presence of 1.5 equivalent of Bu₄NF. However, when these reactions were carried out in the presence of 4 equivalents of Bu₄NF, 3-substituted 1,2-benzisothiazoles were obtained. Additionally, the reaction of phenyl[(3-trimethylsilyl)-2-naphthyl]iodonium triflate with dialkylaminothia-zadienes in the presence of Bu₄NF gave 3-substituted 1,2-naphthisothiazoles. A possible mechaism for the latter reaction involving the trapping of a benzyne intermediate with a nitrile sulfide generated in situ by the reaction of dialkylaminothiazadiene, fluoride ion and trimethylsilyl fluoride is proposed.