Synthesis of 2-Substituted Tryptamines via Cyanide-Catalyzed Imino-Stetter Reaction

Hyung Joo Kim, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we describe the development of a two-step protocol for the synthesis of 2-substituted tryptamine derivatives from 2-aminocinnamyl nitriles and aldehydes. The cyanide-catalyzed imino-Stetter reaction of 2-aminocinnamyl nitriles and aldehydes provided 2-substituted indole-3-acetonitrile derivatives. Subsequent reduction of the nitrile group afforded the desired 2-substituted tryptamine derivatives. The utility of this protocol was demonstrated in the synthesis of a potential inhibitor of 15-lipoxygenase. Furthermore, the resulting 2-substituted indole-3-acetonitriles were converted to several 2,3-disubstituted indole derivatives upon transformation of the nitrile group into other functional groups.

Original languageEnglish
Pages (from-to)2103-2107
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume9
Issue number12
DOIs
Publication statusPublished - 2020 Dec

Keywords

  • Cyanide
  • Imino-Stetter reaction
  • Indoles
  • Nitrile
  • Tryptamines

ASJC Scopus subject areas

  • Organic Chemistry

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