Tandem synthesis of polysubstituted pyridines via the indium(III)-triflate-catalyzed cycloaddition/oxidative aromatization of blaise reaction intermediates with α,β-unsaturated ketones

Zi Xuan, Kris Rathwell, Sang Gi Lee

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A tandem one-pot method for the construction of polysubstituted pyridines with complete control of the substitution pattern has been developed. The zinc bromide β-enamino ester intermediates of the Blaise reaction of simple nitriles with a Reformatsky reagent undergo Michael addition with conjugated ketones in the presence of a catalytic amount of In(OTf)3. Final intramolecular cyclization and oxidative aromatization yields polysubstituted pyridines in this tandem one-pot cascade.

Original languageEnglish
Pages (from-to)1108-1112
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume3
Issue number10
DOIs
StatePublished - Oct 2014

Bibliographical note

Publisher Copyright:
© 2014 Wiley-VCH Verlag GmbH & Co.

Keywords

  • Blaise reaction
  • Indium
  • Pyridines
  • Reformatsky reagent
  • α,β-unsaturated ketones

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