Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines by Two Tandem SNAr Events. Part 2 – The Use of o-[N-(Hetero)aryl]aminomethyl Phenols

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Abstract

As was anticipated based on mechanistic reasoning, bis-nucleophilic o-(arylamino)methyl phenols underwent a facile, base-promoted cyclocondensation with reactivity matched bis-electrophilic (hetero)aromatic substrates to give a rare type of substituted diarene-fused [1.4]oxazepines. This finding further supports the idea of the importance of the Smiles rearrangement in the interim of two SNAr events ultimately leading to the formation of the central cycle in the newly formed tricylic scaffold.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
DOIs
StateE-pub ahead of print - 3 May 2019

Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Nucleophilic aromatic substitution
  • Privileged structures
  • Reactivity-matched synthons
  • Smiles rearrangement
  • [1.4]Oxazepines

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