Base-promoted in situ generation of methyl acrylate from dimethyl 3, 3'-dithiodipropionate. Application To N-alkylation of heterocycles
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.
Hamel
P
Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe-Claire - Dorval, Quebec H9R 4P8, Canada.
Girard
M