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Paper | Regular issue | Vol 43, No. 11, 1996, pp.2397-2407
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7555
■ 2-(Tosylamino)benzyltrimethylammonium Halides as Precursors of 2-Substituted Indoles

Piero Dalla Croce, Raffaella Ferraccioli, and Concetta La Rosa

*Centro C.N.R., Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, via Golgi 19, I-20133 Milano, Italy

Abstract

The reactions of 2-(tosylamino)benzyltrimethylammonium halides (1) with dimethylsulfonium 2-oxo-2-phenylethylide (6b), dimethylsulfonium 2-ethoxy-2-oxo-ethylide (6c) and dimethylsulfonium cyanomethylide (6d) are useful synthetic routes to 2-substituted indoles (8b-d). The relationship between reaction conditions and selectivity is discussed.