Synthesis of All Regioisomers of 2-Arylazaindole-3-acetic Acid Derivatives

Taewook Kim, Ju Hyeon Park, Cheol Jeong, Eunjoon Park, Jong Mu Kim, You Jin Kim, Jung Nyoung Heo, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

Abstract

A novel protocol was developed for synthesizing 2-aryl-sub-stituted azaindole-3-acetic acid derivatives from 2-aminoazacinnamic acid derivatives and aryl aldehydes through an imino-Stetter reaction. Condensation of 2-aminoazacinnamic acid derivatives with aldehydes forms the corresponding aldimines, which are then treated with cyanide to yield the desired 2-aryl-substituted azaindole-3-acetic acid derivatives. Notably, this protocol could be employed for the synthesis of all regioisomers of azaindole-3-acetic acid derivatives by using the appropriate azacinnamic acid derivatives.

Original languageEnglish
Pages (from-to)860-870
Number of pages11
JournalSynthesis (Germany)
Volume56
Issue number5
DOIs
Publication statusPublished - 2023 Sept 19
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2024. Thieme. All rights reserved.

Keywords

  • azacinnamic acid derivatives
  • azaindoles
  • cyanide
  • imino-Stetter reaction
  • regioisomers

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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