Base-Catalysed (4+2)-Annulation Between 2-Nitrobenzofurans and N-Alkoxyacrylamides: Synthesis of [3,2-b]Benzofuropyridinones

Gunda Ananda Rao, Ramani Gurubrahamam, Kwunmin Chen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient protocol for base-catalysed (4+2) annulation between 2-nitrobenzofuran and N-alkoxyacrylamide was developed. The corresponding 1-alkoxy-3,4-dihydrobenzofuro[3,2-b]pyridin-2(1H)-ones were obtained in high to excellent yields by organic base catalysis. In addition, a dearomative nitrotetrahydrobenzofuro[3,2-b]pyridin-2(3H)-ones were also obtained in high yields in the presence of an inorganic base. The advantages of this methodology include easily accessible starting materials, simple operational procedures, broad substrate scope, and synthetically useful yields at milder reaction conditions.

Original languageEnglish
Article numbere202200657
JournalEuropean Journal of Organic Chemistry
Volume2022
Issue number30
DOIs
Publication statusPublished - 2022 Aug 12

Keywords

  • (4+2)-Annulation
  • 2-Nitrobenzofuran
  • Dearomatisation
  • Heterocycle
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Base-Catalysed (4+2)-Annulation Between 2-Nitrobenzofurans and N-Alkoxyacrylamides: Synthesis of [3,2-b]Benzofuropyridinones'. Together they form a unique fingerprint.

Cite this