ChemInform Abstract: Base-Promoted in situ Generation of Methyl Acrylate from Dimethyl 3,3′-Dithiodipropionate. Application to N-Alkylation of Heterocycles.

Abstract

In basic medium, dimethyl 3,3‘-dithiopropionate generates methyl acrylate, which serves in situ as a source of propionate moiety. This property was applied to the alkylation of indoles and other nitrogen heterocycles leading to a series of 3-(heteroaryl-substituted) propionates. A mechanistic rationale for the generation of acrylate is presented along with supportive experimental data.