Synthesis of tetrahydro-β-carbolines via radical cyclization of 2-alkenylthioanilides

Manami Iwadate, Tohru Yamashita, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A synthetic protocol of 1,2,3,4-tetrahydro-β-carbolines from o-alkenylaniline and α-amino acid was developed. Condensation of α-amino acids with 2-alkenylaniline derived from quinoline gave o-alkenylanilides. Conversion of the anilides to thioanilides was effected with Lawesson's reagent in the presence of pyridine, which was crucial to suppress epimerization of the chiral center. After formation of an indole skeleton by radical cyclization, 1,2,3,4-tetrahydro-β-carbolines were obtained via intramolecular N-alkylation.

Original languageEnglish
Pages (from-to)241-249
Number of pages9
JournalHeterocycles
Volume66
Issue number1
DOIs
Publication statusPublished - 2005 Dec 31
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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