Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

Arthur Y. Shaw, Zhigang Xu, Christopher Hulme

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.

Original languageEnglish (US)
Pages (from-to)1998-2000
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number15
DOIs
StatePublished - Apr 11 2012

Keywords

  • 2,4,5-Trisubstituted oxazoles
  • Multicomponent reactions
  • Robinson-Gabriel reaction
  • Ugi reaction
  • Vilsmeier-Haack reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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