Tetrahedron

Functionalisation of the alkoxy group of alkyl aryl ethers. Demethylation, alkylthiolation and reduction of 5-methoxyindoles

C Caubère, P Caubère, P Renard, JG Bizot-Espiart…

Index: Caubere, Catherine; Caubere, Paul; Renard, Pierre; Bizot-Espiart, Jean-Guy; Ianelli, Sandra; et al. Tetrahedron, 1994 , vol. 50, # 47 p. 13433 - 13448

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Citation Number: 10

Abstract

In the presence of A1X3-RSH three kinds of reactions may take place with 5-methoxy indoles: demethylation, alkylthiolation and reduction. The two latter reactions have never been observed to the present, with such reagents. Considerable improvement in the selective demethylation was found when PhCH2SH replaced EtSH previously used in such transformations. Factors leading to selective alkylthiolations or reductions are shown and ...