Base-catalyzed conjugate addition of thiols to indolyl acrylic acids and in situ decarboxylation: An expedient synthesis of functionalized 3-(1-thio)ethyl-1H-indoles

Shijay Gao, Chi Tseng, B. Rama Raju, Chen Hsuan Tsai, Ching Fa Yao

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4 Citations (Scopus)

Abstract

A one-pot, two-step method for the synthesis of 3-(1-thio)ethyl- 1H-indoles is described herein. This simple procedure in-volves the Michael addition of thiols to 3-indoleacrylic acids fol-lowed by in situ decarboxylation of the Michael adduct in the presence of a catalytic amount of K2CO 3 in DMF at 100 °C. The method was found to be fairly general with various thiols and dif-ferent 3-indoleacrylic acids.

Original languageEnglish
Pages (from-to)3201-3205
Number of pages5
JournalSynlett
Issue number19
DOIs
Publication statusPublished - 2009 Dec 21

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Keywords

  • 3-[1-(thio)ethyl]-1H-indole
  • Conjugate addition
  • Decarboxylation
  • Indole
  • Thiol

ASJC Scopus subject areas

  • Organic Chemistry

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