1-(2H-Azirine-2-carbonyl)benzotriazoles: Building blocks for the synthesis of pyrrole-containing heterocycles

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5 Citations (Scopus)

Abstract

A one-pot method was developed for the preparation of 2H-azirine-2-carbonylbenzotriazoles, formed by the reaction of benzotriazole with 2H-azirine-2-carbonyl chlorides, which were generated by the Fe(ii)-catalyzed isomerization of 5-chloroisoxazoles. The Co(ii)-catalyzed reaction of 2H-azirine-2-carbonylbenzotriazoles with 1,3-diketones provides 2-((benzotriazol-1-yl)carbonyl)pyrroles in moderate to good yields. Base-promoted annulations of 2-((benzotriazol-1-yl)carbonyl)pyrroles with aldehydes, ketones, isocyanates and isothiocyanates afford various substituted pyrrolo[1,2-c]oxazole and 1H-pyrrolo[1,2-c]imidazole derivatives in moderate to high yields. The 6-acyl group of these adducts can be removed by triflic acid, giving further new pyrrolo-fused O- and N-heterocycles, such as 6-unsubstituted pyrrolo[1,2-c]oxazol-1(3H)-one and 1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione, while the 6-acetyl substituent of 1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione, when treated with POCl3/pyridine, is transformed into the 6-ethynyl substituent.

Original languageEnglish
Pages (from-to)2283-2296
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number12
DOIs
Publication statusPublished - 28 Mar 2020

Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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