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PHOTOCHEMICAL SYNTHESIS OF NOVEL NAPHTHO[1,2-b]BENZOFURAN DERIVATIVES FROM 2,3-DISUBSTITUTED BENZOFURANS

Boris V. Lichitsky, Constantine V. Milyutin, Valeriya G. Melekhina, Artem N. Fakhrutdinov, Andrey N. Komogortsev, Michail M. Krayushkin

Abstract


A novel approach to the synthesis of naphtho[1,2-b]benzofuran derivatives based on the photochemical reaction of 2,3-disubstituted benzofurans was developed. The studied process includes the photocyclization of the hexatriene system and subsequent aromatization of benzene ring via elimination of water molecule. The starting terarylenes were prepared via a new three-component condensation of phenols, arylglyoxals, and cyclic 1,3-diketones.


Keywords


dibenzo[b,d]furans; naphtho[1,2-b]benzofurans; terarylenes; intramolecular dehydration; photocyclization.

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