Synthesis of fluorescent heterocycles: Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

Guillermo Martinez-Ariza, Bereketab T. Mehari, Ludmila A.G. Pinho, Christopher Foley, Kendall Day, John C Jewett, Christopher Hulme

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

A concise one-pot three-component reaction that affords fluorescent indolizines, benzo[d]pyrrolo[2,1-b]thiazoles, and pyrrolo[1,2-a]pyrazines is reported. The methodology involves the formation of a heterocyclic 1-aza-1,3-diene derived from a Knoevenagel condensation between an aldehyde and 2-methyl-ene-cyano aza-heterocycles, followed by [4 + 1] cycloaddition of acetyl cyanide behaving as a non-classical isocyanide replacement.

Original languageEnglish (US)
Pages (from-to)6076-6079
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number29
DOIs
StatePublished - 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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