Bifunctional building blocks in the Ugi-azide condensation reaction: A general strategy toward exploration of new molecular diversity

Steven Gunawan, Christopher Hulme

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

1,5-Disubstituted tetrazoles are an important drug-like scaffold known for their ability to mimic the cis-amide bond conformation. The scaffold is readily accessible via substitution of the carboxylic acid component of the Ugi multi-component reaction (MCR) with TMSN3 in what is herein denoted the Ugi-azide reaction. This full paper presents a concise, novel, general strategy to access a plethora of new heterocylic scaffolds utilizing tethered aldo/keto-acids/esters in the Ugi-azide reaction followed by a ring closing event that generates novel highly complex bis-heterocyclic lactam-tetrazoles.

Original languageEnglish (US)
Pages (from-to)6036-6046
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number36
DOIs
StatePublished - Sep 28 2013

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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