Double "open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds

Takumi Abe, Haruka Shimizu, Shiori Takada, Takahiro Tanaka, Mai Yoshikawa, Koji Yamada

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double "open and shut" transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.

Original languageEnglish
Pages (from-to)1589-1592
Number of pages4
JournalOrganic Letters
Volume20
Issue number6
DOIs
Publication statusPublished - Mar 16 2018
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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