Highly regioselective synthesis of 2,3-disubstituted 2H-1-benzopyrans: Brønsted acid catalyzed [4+2] cycloaddition reaction with a variety of arylalkynes via ortho-quinone methides

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

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

A highly regioselective one-pot synthesis of 2,3-disubstituted-2H-1-benzopyrans has been developed through Brønsted acid catalyzed [4+2] cycloaddition reaction with a variety of arylalkynes via ortho-quinone methides. A catalytic amount of trifluoromethanesulfonic acid effectively promotes the [4+2] cycloaddition reaction of salicylaldehydes with arylalkynes to afford the corresponding 2H-1-benzopyrans in good yields with high regioselectivities. Treatment of the cycloadduct 2,3-diphenyl-2H-1-benzopyran with some nucleophiles led to 4H-1-benzpyrans and 2H-1-benzopyran according to reagents. The present reactions provide versatile access to functionalized 2,3-disubstituted-2H-1-benzopyrans that would be a useful tool for the synthesis of biologically and photochemically active molecules.

Original languageEnglish
Pages (from-to)6456-6464
Number of pages9
JournalTetrahedron
Volume73
Issue number45
DOIs
Publication statusPublished - Nov 9 2017
Externally publishedYes

Keywords

  • 2H-1-Benzopyran
  • Brønsted acid catalyst
  • Regioselective synthesis
  • [4+2] Cycloaddition
  • ortho-Quinone methide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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