Synthesis of peptidomimetics, δ- And ε-lactam tetrazoles

Steven Gunawan, Kristen Keck, Alex Laetsch, Christopher Hulme

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1′-carbonyldiimidazole-mediated intramolecular amide formation. Expansion to ε-lactam tetrazole scaffolds was accomplished using methyl 6-oxoheptanoate via the same Ugi-azide reaction followed by basic hydrolysis and SOCl2 activation to enable lactam formation.

Original languageEnglish (US)
Pages (from-to)601-606
Number of pages6
JournalMolecular Diversity
Volume16
Issue number3
DOIs
StatePublished - Aug 2012

Keywords

  • 1,5-disubstitutedtetrazoles
  • Multi-component reactions (MCRs)
  • Ugi reaction

ASJC Scopus subject areas

  • Catalysis
  • Information Systems
  • Molecular Biology
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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