On the formation of seven-membered rings by arene-ynamide cyclization

Bogdan R. Brutiu, Wilhelm Andrei Bubeneck, Olivera Cvetkovic, Jing Li, Nuno Maulide

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Abstract: A Brønsted acid-catalyzed selective arene-ynamide cyclization is described. This reaction proceeds via a keteniminium intermediate and enables the preparation of seven-membered ring enamide products. Mechanistic studies uncover an unusual product inhibition behavior. Graphical abstract: [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)3-10
Number of pages8
JournalMonatshefte fur Chemie
Volume150
Issue number1
DOIs
Publication statusPublished - 2019 Jan 1
Externally publishedYes

Keywords

  • Brønsted acid
  • Catalysis
  • Heterocycles
  • Strained molecules

ASJC Scopus subject areas

  • Chemistry(all)

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