“Isocyanide-less” Ugi/Intramolecular Diels-Alder reaction of 5-hydroxymethylfurfural

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6 Scopus citations

Abstract

The one-pot, three-step, four-component Ugi-IMDAF reaction with 5-hydroxymethylfurfural provides simple access to hydroxymethyl-substituted epoxyisoindolones in a diastereoselective and stereospecific manner. The protocol avoids the transfer or isolation of isocyanides, and the broad scope was illustrated by the synthesis of 22 different compounds bearing various substituents on the heterocyclic core.

Original languageEnglish
Pages (from-to)1578-1581
JournalTetrahedron Letters
Volume60
Issue number24
Early online date20 May 2019
DOIs
StatePublished - 13 Jun 2019

Scopus subject areas

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

Keywords

  • 5-Hydroxymethylfurfural
  • Diels-Alder reaction
  • Isocyanide-based multicomponent reaction
  • Ugi reaction
  • PRODUCTS
  • TRICYCLIC NITROGEN-HETEROCYCLES
  • UGI REACTION
  • SKELETAL

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