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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

Author:
Tanaka, Kenta, Sukekawa, Mayumi, Shigematsu, Yosuke, Hoshino, Yujiro, Honda, Kiyoshi
Source:
Tetrahedron 2017 v.73 pp. 6456-6464
ISSN:
0040-4020
Subject:
Lewis bases, chemical structure, cycloaddition reactions, organic compounds, regioselectivity
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.
Agid:
5837333