Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines

Arthur Y. Shaw, Christine R. Denning, Christopher Hulme

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

A facile and expeditious synthetic approach for the synthesis of α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2.

Original languageEnglish (US)
Pages (from-to)4151-4153
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number32
DOIs
StatePublished - Aug 8 2012

Keywords

  • Arylglyoxals
  • Microwave-assisted
  • Selenium dioxide
  • α-Ketoamides

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines'. Together they form a unique fingerprint.

  • Cite this