One-Pot Synthesis of 2-Acetyl-1 H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines


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Kanova N., Dündar B. A. , Kelgokmen Y., Zora M.

Journal of Organic Chemistry, vol.86, no.9, pp.6289-6304, 2021 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 86 Issue: 9
  • Publication Date: 2021
  • Doi Number: 10.1021/acs.joc.1c00077
  • Journal Name: Journal of Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, Compendex, EMBASE, MEDLINE
  • Page Numbers: pp.6289-6304
  • Middle East Technical University Affiliated: Yes

Abstract

© 2021 American Chemical Society.A one-pot two-step protocol for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic β-enaminones was described. When treated with zinc chloride in refluxing chloroform, N-propargylic β-enaminones produced in situ 2-methylene-2,3-dihydro-1,4-oxazepines, which, upon further refluxing in methanol with zinc chloride, afforded 2-acetyl-1H-pyrroles. The process was found to be general for a wide variety of N-propargylic β-enaminones and yielded a diverse range of 2-acetyl-1H-pyrroles in good to high yields with large substrate scope and good functional group tolerance. This operationally easy method may provide a rapid access to functionalized 2-acetyl-1H-pyrroles of pharmacological interest.