Solid-phase synthesis of quinoxaline, thiazine, and oxazine analogs through a benzyne intermediate

Seth Dixon, Xiaobing Wang, Kit Lam, Mark J. Kurth

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

A solid-phase synthetic route to quinoxaline, thiazine, and oxazine analogs is described. N-Alloc-3-amino-3-(2,4-difluoro-5-nitrophenyl)propanoic acid was tethered to Rink resin via its carboxylic acid group. The 4-arylfluorine was displaced with a primary amine, alcohol, or thiol to create, respectively, a resin bound aniline, phenol, or thiophenol derivative with one diversity element and one single atom (e.g., N, S, or O) diversity point. A fused heterocyclic system was subsequently created via a benzyne heterocyclization initiated by dehydrofluorination with strong base. Acid treatment released the desired products in high yield and moderate purity.

Original languageEnglish (US)
Pages (from-to)7443-7446
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number43
DOIs
StatePublished - Oct 24 2005

Keywords

  • Benzyne
  • Oxazine
  • Quinoxaline
  • Solid phase
  • Thiazine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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