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 Citations (Scopus)

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

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Cycloaddition
pyrazines
Cycloaddition Reaction
Cyanides
cycloaddition
cyanides
dienes
aldehydes
Indolizines
cascades
condensation
methodology
Pyrazines
Thiazoles
synthesis
Aldehydes
Condensation

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of fluorescent heterocycles : Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide. / Martinez-Ariza, Guillermo; Mehari, Bereketab T.; Pinho, Ludmila A.G.; Foley, Christopher; Day, Kendall; Jewett, John C; Hulme, Christopher.

In: Organic and Biomolecular Chemistry, Vol. 15, No. 29, 2017, p. 6076-6079.

Research output: Contribution to journalArticle

Martinez-Ariza, Guillermo ; Mehari, Bereketab T. ; Pinho, Ludmila A.G. ; Foley, Christopher ; Day, Kendall ; Jewett, John C ; Hulme, Christopher. / Synthesis of fluorescent heterocycles : Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide. In: Organic and Biomolecular Chemistry. 2017 ; Vol. 15, No. 29. pp. 6076-6079.
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