Base-promoted in situ generation of methyl acrylate from dimethyl 3,3 '-dithiodipropionate. Application to N-alkylation of heterocycles

Authors
Hamel, P Girard, M
Citation
P. Hamel et M. Girard, Base-promoted in situ generation of methyl acrylate from dimethyl 3,3 '-dithiodipropionate. Application to N-alkylation of heterocycles, J ORG CHEM, 65(10), 2000, pp. 3123-3125
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
10
Year of publication
2000
Pages
3123 - 3125
Database
ISI
SICI code
0022-3263(20000519)65:10<3123:BISGOM>2.0.ZU;2-0
Abstract
In basic medium, dimethyl 3,3'-dithiopropionate generates methyl acrylate, which serves in situ as a source of propionate moiety. This property was ap plied to the alkylation of indoles and other nitrogen heterocycles leading to a series of 3-(heteroaryl-substituted) propionates. A mechanistic ration ale for the generation of acrylate is presented along with supportive exper imental data.