Concise route to a series of novel 3-(tetrazol-5-yl)quinoxalin-2(1H)-ones

Steven Gunawan, Gary Nichol, Christopher Hulme

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

This Letter presents a novel three step solution phase protocol to synthesize 3-(tetrazol-5-yl)quinoxalin-2(1H)-ones. The strategy utilizes ethyl glyoxalate and mono-N-Boc-protected-o-phenylenediamine derivatives in the Ugi-Azide multi-component reaction (MCR) to generate a unique 1,5-disubstituted tetrazole. Subsequent acid treatment stimulates a simultaneous Boc deprotection and intramolecular cyclization leading to bis-3,4-dihydroquinoxalinone tetrazoles. Direct oxidation using a stable solid-phase radical catalyst (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) with ceric ammonium nitrate (CAN) in catalytic fashion initiating aerobic oxidation, completes the entire procedure to generate a series of original unique bis-quinoxalinone tetrazoles. The method was also expanded to produce a bis-benzodiazepine tetrazole.

Original languageEnglish (US)
Pages (from-to)1664-1667
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number13
DOIs
StatePublished - Mar 28 2012

Keywords

  • Isonitrile
  • Multi-component reaction
  • Quinoxalinone
  • Tetrazole
  • Ugi

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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