Sequential Ugi/Strecker reactions via microwave assisted organic synthesis: Novel 3-center-4-component and 3-center-5-component multi-component reactions

Thierry Masquelin, Hai Bui, Bob Brickley, Gregory Stephenson, John Schwerkoske, Christopher Hulme

Research output: Contribution to journalArticle

63 Scopus citations

Abstract

Two novel one-step microwave mediated syntheses of arrays of 3-iminoaryl-imidazo[1,2-a]pyridines and imidazo[1,2-a]pyridyn-3-ylamino-2- acetonitriles are reported. Reactions are performed under microwave condition in methanol by simply mixing α-amino-pyridines, aldehydes, and trimethylsilylcyanide (TMSCN) with distinct reagent stoichiometries, catalyzed by polymer-bound scandium triflate, to afford either product. Furthermore, functionally different aldehydes were shown to proceed to different end-points, adding an extra caveat to the studies. The new methodology represents examples of both formal 3-center-4-component and 3-center-5-component multi-component reactions.

Original languageEnglish (US)
Pages (from-to)2989-2991
Number of pages3
JournalTetrahedron Letters
Volume47
Issue number17
DOIs
StatePublished - Apr 24 2006
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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