α-Keto Thioesters as Building Blocks for Accessing γ-Hydroxybutenolides and Oxazoles

Kanchan Mal, Indrajit Das

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

α-Keto thioesters, with two electrophilic carbon centres, have been found to react differently with β-keto esters and isocyanoacetates. They undergo base induced Knoevenagel-type condensation on the keto carbonyl group with β-keto esters, followed by intramolecular cyclization and water addition leads to highly substituted γ-hydroxybutenolides. On the other hand, substituted oxazole derivatives have been obtained using isocyanoacetates via nucleophilic displacement on the thioester carbonyl followed by intramolecular cyclization. Further functionalization of the γ-hydroxybutenolides is also demonstrated via a BF3.OEt2-mediated cation-driven nucleophilic addition of terminal alkynes to access multiply substituted butenolides. (Figure presented.).

Original languageEnglish
Pages (from-to)2692-2698
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number15
DOIs
StatePublished - 7 Aug 2017
Externally publishedYes

Keywords

  • oxazoles
  • rearrangement
  • synthetic methods
  • α-keto thioesters
  • γ-hydroxybutenolides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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