A One-Pot Method to Prepare 4,5-Benzotropones and 2,3,4,5-Dibenzotropones

Dedicated to Professor Guoqiang Lin on the occasion of his 80^th birthday.

Abstract

An extremely simple method is developed to prepare 4,5-benzotropones and 2,3,4,5-dibenzotropones via one-pot cycloaddition reactions of alkynes with naphthoquinones and dibenzoquinones mediated by BF₃·Et₂O. Various mono- and disubstituted phenylacetylenes, multisubstituted 1,2-naphthoquinones and dibenzoquinone substrates are investigated. In addition, a scale-up synthesis of 7-phenyl-5H-dibenzo[a,c][7]annulen-5-one and further derivation of 7-(4-fluorophenyl)-5H-dibenzo[a,c][7]annulen-5-one are explored.

Key words

4,5-benzotropones - 2,3,4,5-dibenzotropones - BF₃·Et₂O-mediated reaction - dibenzoquinones - 1,2-naphthoquinones

Publication History

Received: 11 December 2022

Accepted after revision: 12 January 2023

Accepted Manuscript online:
12 January 2023

Article published online:
08 February 2023

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