Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies

Derek A. Leas, Jianbo Wu, Edward L. Ezell, Jered C. Garrison, Jonathan L. Vennerstrom, Yuxiang Dong

Research output: Contribution to journalArticle

Abstract

We describe a new 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU)-mediated coupling reaction to produce 2-imino benzo[e]-1,3-oxazin-4-ones from salicylic acids and anilines. Mechanistic studies support a reaction pathway in which HATU mediates carbon transfer to the initially formed salicylanilides to form in succession reactive tetramethylisouronium and N-acyl(dimethyl)isouronium intermediates, which then undergo imine-iminium exchange to generate the desired oxazinones.

Original languageEnglish (US)
Pages (from-to)781-787
Number of pages7
JournalACS Omega
Volume3
Issue number1
DOIs
StatePublished - Jan 31 2018

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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