Regioselective Synthesis of Benzazetines and Indoles from Alkenylanilides and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate
Chemistry Letters2006Vol. 35(10), pp. 1122–1123
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Abstract
Abstract Regioselective synthesis of benzazetines and indoles from o-alkenylanilides was achieved. The reaction of o-vinylbenzanilide with dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) gave the corresponding benzazetine in 92% yield, whereas the reaction of o-vinyl-N-p-toluenesulfonylanilide gave N-tosylindoline in 77% yield. 3-Methy-N-p-tosylindole was directly synthesized by the reaction of o-isopropenyl-N-p-tosylanilide with dimethyl disulfide and methyl triflate in 85% yield.
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