Regioselective one-pot synthesis of 2,3-diaryl-2H-1-benzopyrans via Brønsted acid-catalyzed [4+2] cycloaddition of salicylaldehydes with diarylacetylenes

Kenta Tanaka, Yosuke Shigematsu, Mayumi Sukekawa, Yujiro Hoshino, Kiyoshi Honda

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

A regioselective one-pot synthesis of 2,3-diaryl-2H-1-benzopyrans from easily available various diarylacetylenes and salicylaldehydes via Brønsted acid-catalyzed [4+2] cycloaddition has been developed. High regioselectivity was observed in the reaction to afford 2-(electron-rich aryl)-3-(electron-poor aryl)-2H-1-benzopyrans in good yields. The present reaction provides versatile access to functionalized 2,3-diaryl-2H-1-benzopyrans, which would be useful as key intermediates for the synthesis of biologically and photochemically active molecules.

Original languageEnglish
Pages (from-to)5914-5918
Number of pages5
JournalTetrahedron Letters
Volume57
Issue number52
DOIs
Publication statusPublished - 2016
Externally publishedYes

Keywords

  • Benzopyrans
  • Brønsted acid catalyst
  • ortho-Quinonemethide
  • Regioselective synthesis
  • [4+2] cycloaddition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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