Combinatorial Chemistry Review

Preparation of Indoles and Oxindoles from N-(tret-Butoxycarbonyl)-2-alkilanilines

Robin D. Clark, Joseph M. Muchowski, Lawrence E. Fisher, Lee A. Flippin, David B. Repke, Michel Souchet. Synthesis 1991, p.871-877

Despite the many methods which have been devised for the synthesis in indoles over the past 120 years, the development of milder, more rediospecific methods continues to be an active area of investigation. Notable recent contributions have included a number of indole syntheses which proceed from derivatives of 2-alkylanilines and which extend and earlier methods such as the Madelung synthesis. We recently presented preliminary results on an indole synthesis based on the condensation of the dilithio species derived from N-(tret-Butoxycarbonyl)-2-alkilanilines with amides. In this paper we present details and further extensions of this methodology including application to the synthesis of oxindoles (indol-2(3H)-ones).

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