A facile and concise route toward the synthesis of novel imidazo-tetrazolodiazepinones via post-condensation modifications of the Ugi-azide adduct

Federico Medda, Guillermo Martinez-Ariza, Christopher Hulme

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

Abstract This Letter describes novel methodology for the rapid assembly of unprecedented and likely biologically relevant imidazo-tetrazolodiazepinones. The product of a TMSN<inf>3</inf>-Ugi multi-component reaction is treated with an excess of isocyanate to generate 1,5-disubstituted tetrazolo-hydantoins functionalized with an internal-masked amino nucleophile previously introduced by the isocyanide input. Final products are obtained in good overall yields after microwave irradiation of the tetrazolo-hydantoin in acidic media. This methodology allows the production of complex polycyclic compounds in a mere three synthetic steps.

Original languageEnglish (US)
Article number46572
Pages (from-to)5295-5298
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number38
DOIs
StatePublished - Sep 16 2015

Keywords

  • Diazepinone
  • Hydantoin
  • Multicomponent reaction
  • Tetrazole
  • UDC
  • Ugi reaction

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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