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Issue 13, 2020
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Synthesis of substituted naphtho[1,2-b]benzofuran-7(8H)-ones via photoinduced rearrangement of 4H-chromen-4-one derivatives

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Abstract

A simple and efficient method was developed for the synthesis of substituted naphtho[1,2-b]benzofuran-7(8H)-ones based on the photorearrangement reaction of 4H-chromen-4-one derivatives. The studied reaction includes the photocyclization of the hexatriene system, [1,9]-H-sigmatropic rearrangement and heterocyclic ring opening. The starting terarylenes were prepared via a new three-component tandem condensation of 3-(dimethylamino)-1-(2-hydroxyaryl)prop-2-en-1-ones, arylglyoxals and cyclic 1,3-diketones.

Graphical abstract: Synthesis of substituted naphtho[1,2-b]benzofuran-7(8H)-ones via photoinduced rearrangement of 4H-chromen-4-one derivatives

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Article information


Submitted
22 Jan 2020
Accepted
11 Mar 2020
First published
11 Mar 2020

Org. Biomol. Chem., 2020,18, 2501-2509
Article type
Paper

Synthesis of substituted naphtho[1,2-b]benzofuran-7(8H)-ones via photoinduced rearrangement of 4H-chromen-4-one derivatives

B. V. Lichitskii, V. G. Melekhina, A. N. Komogortsev, C. V. Milyutin, A. N. Fakhrutdinov, Y. O. Gorbunov and M. M. Krayushkin, Org. Biomol. Chem., 2020, 18, 2501
DOI: 10.1039/D0OB00149J

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