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Synthesis 2021; 53(14): 2449-2456
DOI: 10.1055/a-1396-8123
DOI: 10.1055/a-1396-8123
paper
Oxidative Dimerization of 1Н-Benzo[f]chromenes: Synthesis of Benzannulated Analogues of Spirobiflavonoids Welwitschins E and F
The work was supported by the Russian Foundation for Basic Research (Grant No. 18-33-20249).
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-chromenesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1396-8123.
- Supporting Information
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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