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Note | Regular issue | Vol 71, No. 2, 2007, pp.419-428
Published online, 26th December, 2006
DOI: 10.3987/COM-06-10933
■ Synthesis of 5-Substituted 4,5,6,7-Tetrahydroindoles from Cyclohexanones

Chang Kiu Lee,* In-Sook Han Lee, and Wayland E. Noland

*Department of Chemistry, Kangwon National University, 192-1 Hyoja-2-dong, Chuncheon, Kangwon 200-701, Korea

Abstract

5-Substituted 4,5,6,7-tetrahydroindoles were prepared from 4-substituted cyclohexanones in three steps: conversion to an enol silyl ether, introduction of a formylmethyl group at 2-C, and the Paal-Knorr pyrrole synthesis by reacting the 1,4-dicarbonyl compounds with ammonia. The substituents are H, methyl, ethyl, tert-butyl, methoxy, and phenyl.