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 Citations (Scopus)

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

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Benzodiazepinones
Azides
Cyclization
Benzodiazepines
phenylisocyanide
glyoxylic acid

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of tetrazolo-fused benzodiazepines and benzodiazepinones by a two-step protocol using an Ugi-azide reaction for initial diversity generation. / Gunawan, Steven; Ayaz, Muhammad; De Moliner, Fabio; Frett, Brendan; Kaiser, Christine; Patrick, Nina; Xu, Zhigang; Hulme, Christopher.

In: Tetrahedron, Vol. 68, No. 27-28, 08.07.2012, p. 5606-5611.

Research output: Contribution to journalArticle

Gunawan, Steven ; Ayaz, Muhammad ; De Moliner, Fabio ; Frett, Brendan ; Kaiser, Christine ; Patrick, Nina ; Xu, Zhigang ; Hulme, Christopher. / Synthesis of tetrazolo-fused benzodiazepines and benzodiazepinones by a two-step protocol using an Ugi-azide reaction for initial diversity generation. In: Tetrahedron. 2012 ; Vol. 68, No. 27-28. pp. 5606-5611.
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