Molecular Diversity

, Volume 16, Issue 3, pp 601–606

Synthesis of peptidomimetics, δ- and \({\varepsilon}\)-lactam tetrazoles

  • Steven Gunawan
  • Kristen Keck
  • Alex Laetsch
  • Christopher Hulme
Short Communication

DOI: 10.1007/s11030-012-9373-2

Cite this article as:
Gunawan, S., Keck, K., Laetsch, A. et al. Mol Divers (2012) 16: 601. doi:10.1007/s11030-012-9373-2

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 \({\varepsilon}\)-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.

Keywords

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

Supplementary material

11030_2012_9373_MOESM1_ESM.pdf (367 kb)
ESM 1 (PDF 367 kb)

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Steven Gunawan
    • 1
  • Kristen Keck
    • 1
  • Alex Laetsch
    • 1
  • Christopher Hulme
    • 1
  1. 1.BIO5 Oro ValleyThe University of ArizonaOro ValleyUSA

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