Epoxyanthracene Derivatives and Dicarbonylation on Benzene Ring via Hexadehydro-Diels–Alder (HDDA) Derived Benzynes with Oxazoles

Abstract

A capture reaction of hexadehydro-Diels–Alder (HDDA) derived benzyne with various substituted oxazoles is reported. With methyl, hydrogen, or phenyl as the substituent at 2-position of oxazole, tetraynes afforded epoxyanthracene derivatives or underwent dicarbonylation on benzene ring. The reaction does not require any catalyst or additive. The mechanism behind the reaction was investigated. The obtained polycyclic product structure has potential application value in optoelectronic materials. The availability of dicarbonylated arene implies the uniqueness of HDDA benzyne reaction compared with traditional benzyne.

Key words

HDDA - oxazole - epoxyanthracene - dicarbonylation - Diels–Alder reaction

Publication History

Received: 27 July 2021

Accepted after revision: 30 September 2021

Accepted Manuscript online:
01 October 2021

Article published online:
10 November 2021

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