Synthesis of 2-Aryl-Substituted Indole-3-acetic Acid Derivatives via Intramolecular Imino-Stetter Reaction of Aldimines with Cyanide

A general method to generate umpolung of aldimines with cyanide was developed via the addition of cyanide to aldimines followed by a proton transfer from the carbon atom to the nitrogen atom in the resulting cyanide adducts. This novel method was successfully applied to the first imino‐Stetter react...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-05, Vol.358 (10), p.1566-1570
Main Authors: Lee, Seong Jong, Seo, Hong-Ahn, Cheon, Cheol-Hong
Format: Article
Language:English
Subjects:
2-arylindole-3-acetic acid derivatives
aldimines
Carbon
Catalysis
cyanide
Cyanides
Derivatives
imino-Stetter reaction
Inhibitors
Nitrogen atoms
Synthesis
Synthesis (chemistry)
umpolung
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Summary:A general method to generate umpolung of aldimines with cyanide was developed via the addition of cyanide to aldimines followed by a proton transfer from the carbon atom to the nitrogen atom in the resulting cyanide adducts. This novel method was successfully applied to the first imino‐Stetter reaction of aldimines obtained from 2‐aminocinnamic acid derivatives and aromatic aldehydes with cyanide, affording 2‐aryl‐substituted indole‐3‐acetic acid derivatives. Furthermore, the usefulness of this method was successfully demonstrated by the synthesis of an FPTase inhibitor, one of the biologically important 2‐arylindole‐3‐acetic acid derivatives.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600155