A robust protocol for the synthesis of quinoxalines and 5 H -benzo[ e ][1,4]diazepines via the acidless Ugi reaction

Muhammad Ayaz, Guillermo Martinez-Ariza, Christopher Hulme

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

Concise two-step, one-pot protocols for the syntheses of quinoxalines and 5H-benzo[e][1,4]diazepines are reported. An 'acidless' Ugi reaction followed by a Boc-deprotection-cyclization sequence is shown to produce arrays of both functionalized scaffolds in good yield. Mono-N-Boc-protected diamines are employed to access quinoxalines and an analogous benzylic amine affords access to 5H-benzo[e][1,4]diazepines in conjunction with supporting reagents in the 'acidless' Ugi reaction. Both methodologies are robust, straightforward, and allow installation of at least three points of diversity in the resulting scaffolds.

Original languageEnglish (US)
Article number8037
Pages (from-to)1680-1684
Number of pages5
JournalSynlett
Volume25
Issue number12
DOIs
StatePublished - Jul 2014

Keywords

  • Ugi
  • benzodiazepines
  • combinatorial chemistry
  • multicomponent reaction
  • quinoxalines

ASJC Scopus subject areas

  • Organic Chemistry

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