posted on 2016-08-03, 00:00authored byHong-Ahn Seo, Cheol-Hong Cheon
A new
method for the synthesis of 2-vinylindole-3-acetic acid derivatives
from aldimines, which are derived from 2-aminocinnamic acid derivatives
and α,β-unsaturated aldehydes, via a cyanide-catalyzed
imino-Stetter reaction is described. Various types of 2-aminocinnamic
acid derivatives and α,β-unsaturated aldehydes could be
used in this protocol, and the desired 2-vinyl substituted indole-3-acetic
acid derivatives were obtained in high yields. This cyanide-catalyzed
imino-Stetter reaction was further extended to the preparation of
indole-3-acetic acid derivatives bearing a carboxylic acid functionality
at the 2-position, using aldimines obtained from glyoxylates and 2-aminocinnamic
acid derivatives.