Brook Rearrangement as Trigger for Dearomatization Reaction: Synthesis of Non-Aromatic N-Heterocycles**

Rajarshi Mondal, Mohamed Agbaria, Orit Cohen, Zackaria Nairoukh*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The [1,2]-Brook rearrangement stands as a potent technique for constructing complex molecules. In this study, we showcase its power in the dearomatization of aromatic N-heterocycles. Through a concise four-step process that integrates lithiation, nucleophilic addition, Brook rearrangement and dearomatization reaction, we demonstrate a versatile strategy for generating diverse non-aromatic N-heterocycles which exhibit ambident reactivities. Various acyl silanes, halo-pyridines, and quinolines have been explored within this context. The synthetic utility of this methodology is demonstrated through the construction of complex architectures.

Original languageAmerican English
Article numbere202303588
JournalChemistry - A European Journal
Volume30
Issue number3
DOIs
StatePublished - 11 Jan 2024

Bibliographical note

Publisher Copyright:
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Keywords

  • Brook rearrangement
  • dearomatization
  • heterocycles
  • multicomponent reaction
  • synthetic methods

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