Regioselective Synthesis of Benzazetines and Indoles from Alkenylanilides and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate
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Regioselective synthesis of benzazetines and indoles from <I>o</I>-alkenylanilides was achieved. The reaction of <I>o</I>-vinylbenzanilide with dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) gave the corresponding benzazetine in 92% yield, whereas the reaction of <I>o</I>-vinyl-<I>N</I>-<I>p</I>-toluenesulfonylanilide gave <I>N</I>-tosylindoline in 77% yield. 3-Methy-<I>N</I>-<I>p</I>-tosylindole was directly synthesized by the reaction of <I>o</I>-isopropenyl-<I>N</I>-<I>p</I>-tosylanilide with dimethyl disulfide and methyl triflate in 85% yield.
- Chemistry Letters
Chemistry Letters 35(10), 1122-1123, 2006-10-05
The Chemical Society of Japan