Sequencing Groebke-Blackburn-Bienaymé and Aza-Michael Addition Reactions: A Modular Strategy for Accessing a Diverse Collection of Constrained Benzoxazepine and Imidazopyrazine Systems

Vunnam Srinivasulu, Farah Al-Marzooq, Mohamad Hamad, Monther A. Khanfar, Mani Ramanathan, Nelson C. Soares, Taleb H. Al-Tel

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

We present a divergent strategy that permits access to diversely functionalized benzoxazepinium scaffolds fused to various heterocycles. The described strategy features a one-pot combination of the Groebke-Blackburn-Bienaymé reaction and an aza-Michael addition. Methyl (E)-4-(2-formylphenoxy)but-2-enoate and its derivatives are utilized as central elements in this cascade. These building blocks are reacted with a variety of functionalized amino-azines and tert -butyl isocyanide under ytterbium triflate [Yb(OTf) 3] catalysis. The ensuing cascade represents a rapid, modular and atom-economic process that leads to the construction of a diverse collection of constrained benzoxazepinium systems from a wide substrate scope.

Original languageEnglish
Pages (from-to)1911-1922
Number of pages12
JournalSynthesis
Volume53
Issue number11
DOIs
Publication statusPublished - Jun 2 2021

Keywords

  • Groebke-Blackburn-Bienaymé
  • aza-Michael addition
  • benzoxazepines
  • diversity-oriented synthesis
  • indolopyrazines
  • modular synthesis
  • multicomponent reactions

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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