Synthesis of 2-Vinylindole-3-Acetic Acid Derivatives via Cyanide-Catalyzed Imino-Stetter Reaction.

J Org Chem

Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea.

Published: September 2016

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.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.6b01621DOI Listing

Publication Analysis

Top Keywords

acid derivatives
28
cyanide-catalyzed imino-stetter
12
imino-stetter reaction
12
2-aminocinnamic acid
12
synthesis 2-vinylindole-3-acetic
8
acid
8
2-vinylindole-3-acetic acid
8
derivatives αβ-unsaturated
8
αβ-unsaturated aldehydes
8
indole-3-acetic acid
8

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!