Acetyl cyanide as a cyanide source in a tandem catalyst-free modified Groebke-Blackburn-Bienaymé [4+1]-cycloaddition-Strecker cascade

Guillermo Martinez-Ariza, Jose Nunez-Rios, Yeon Sun Lee, Christopher Hulme

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A concise one-pot 3-step cascade reaction to biologically significant imidazo[1,2-a]heterocycles is described. The methodology utilizes acetyl cyanide as a non-classical isocyanide replacement for TMSCN in a microwave-assisted [4+1] cycloaddition (the Groebke-Bienaymé-Blackburn reaction) followed by a Strecker reaction under catalysis free conditions. The methodology proceeds with operational simplicity, short reaction times, and high bond forming efficiency.

Original languageEnglish (US)
Pages (from-to)1038-1040
Number of pages3
JournalTetrahedron Letters
Volume56
Issue number8
DOIs
StatePublished - Feb 18 2015

Fingerprint

Cycloaddition
Cycloaddition Reaction
Cyanides
Catalysts
Microwaves
Catalysis
trimethylsilyl cyanide

Keywords

  • Bicyclic heterocycles
  • Groebke-Blackburn-Bienaymé
  • Imidazopyridine
  • Multicomponent reaction
  • Strecker

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Acetyl cyanide as a cyanide source in a tandem catalyst-free modified Groebke-Blackburn-Bienaymé [4+1]-cycloaddition-Strecker cascade. / Martinez-Ariza, Guillermo; Nunez-Rios, Jose; Lee, Yeon Sun; Hulme, Christopher.

In: Tetrahedron Letters, Vol. 56, No. 8, 18.02.2015, p. 1038-1040.

Research output: Contribution to journalArticle

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AU - Lee, Yeon Sun

AU - Hulme, Christopher

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