Synthesis of tetrazolo-fused benzodiazepines and benzodiazepinones by a two-step protocol using an Ugi-azide reaction for initial diversity generation

Steven Gunawan, Muhammad Ayaz, Fabio De Moliner, Brendan Frett, Christine Kaiser, Nina Patrick, Zhigang Xu, Christopher Hulme

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

A two-step strategy for the synthesis of arrays of tricyclic tetrazolo-fused benzodiazepines and benzodiazepinones has been investigated. The protocol uses ortho-N-Boc phenylisocyanides and phenylglyoxaldehydes or ethyl glyoxylate in the four-component Ugi-azide reaction to afford MCR (MultiComponent Reactions) derived adducts equipped with the desired diversity inputs. A subsequent acidic treatment (TFA/DCE) allows a simultaneous deprotection-cyclization leading to the final products.

Original languageEnglish (US)
Pages (from-to)5606-5611
Number of pages6
JournalTetrahedron
Volume68
Issue number27-28
DOIs
StatePublished - Jul 8 2012

Keywords

  • Benzodiazepines
  • Benzodiazepinones
  • TMS-N
  • Tetrazoles
  • Ugi reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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