Synthesis of 4-arylethynyl-2-methyloxazole derivatives as mGluR5 antagonists for use in the treatment of drug abuse

Yasuyoshi Iso, Alan P. Kozikowski

Research output: Contribution to journalArticlepeer-review

Abstract

In structure-activity relationship studies directed toward the use of mGluR5 antagonists in the treatment of drug abuse, we sought a convenient means for gaining access to the oxazole analogues of MTEP. Toward this end, the aldehyde group in 2-methyloxazole-4-carboxaldehyde was successfully converted to a trimethylsilylethynyl group via the preparation of a dibromoolefin, conversion to acetylide using NaHMDS and MeLi, and trapping with TMSCl. The resulting versatile intermediate, 2-methyl-4-[(trimethylsilyl)ethynyl]oxazole, was subjected to a modified Sonogashira coupling reaction involving an in situ desilylation reaction with Bu4NF and palladium-catalyzed coupling with an aryl or heteroaryl iodide to give the desired oxazole analogues.

Original languageEnglish (US)
Article numberM04105SS
Pages (from-to)243-246
Number of pages4
JournalSynthesis
Issue number2
DOIs
StatePublished - Jan 18 2006

Keywords

  • Alkynes
  • Cross-coupling
  • Cyclizations
  • Lithiation
  • Palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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