Synthesis of Halogenated Cyclic Enamines from Cyclic N-2-En-4-ynyl-N-1-ynylamides and N-Propargyl-N-1-ynylamides via a Tandem Iron Halide Promoted N-to-C Shift-Aza-Prins Cyclization Sequence

Hsin Hui Lin, Tai Ching Chiang, Rong Xuan Wu, Yi Mei Chang, Hao Wen Wang, Ssu Ting Liu, Ming-Chang P. Yeh

Research output: Contribution to journalArticle

Abstract

A facile and efficient N-to-C allyl shift-aza-Prins cyclization sequence of cyclic N-2-en-4-ynyl-N-1-ynylamides is promoted by iron(III) chloride, generating chloro-containing bridged bicyclic enamines in minutes and in high yields. This reaction involves an unprecedented formation of a ketenimine via Fe(III)-mediated N-to-C allyl rearrangement, followed by aza-Prins cyclization. This sequence can also be applied to the generation of brominated cyclobutenamine derivatives using Fe(III) bromide and N-propargyl-N-1-ynylamides. (Figure presented.).

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusPublished - 2019 Jan 1

Keywords

  • Cyclization
  • Halogenation
  • Rearrangement

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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