Oxidative Dimerization of 1Н-Benzo[f]chromenes: Synthesis of Benzannulated Analogues of Spirobiflavonoids Welwitschins E and F

Abstract

A new oxidative transformation of 1H-benzo[f]chromenes into spirodimers under the action of selenium dioxide was discovered, leading to spirodimers, which are dibenzannulated analogues of naturally occurring welwitschins E and F. In the reaction, both MnO₂ and I₂O₅ can also be used as an oxidant. The protocol has advantages of mild reaction conditions and simple operation. At the same time, oxidation of 1H-benzo[f]chromenes with (diacetoxyiodo)benzene is accompanied by the formation of 3,3′-bibenzo[f]chromene as a dimer of a different structure. It was also found that 4H-chromenes under the action of various oxidants are cleaved to give chalcone.

Key words

oxidation - dimerization - 1Н-benzo[f]chromenes - spirobiflavonoids - welwitschins - selenium dioxide - (diacetoxyiodo)benzene - 4Н-chromenes

Publication History

Received: 26 November 2020

Accepted after revision: 22 February 2021

Accepted Manuscript online:
22 February 2021

Article published online:
22 March 2021

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