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

Authors

  • Boris V. Lichitsky N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Constantine V. Milyutin N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Valeriya G. Melekhina N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Artem N. Fakhrutdinov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Andrey N. Komogortsev N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Michail M. Krayushkin N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

DOI:

https://doi.org/10.1007/5983

Keywords:

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

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.

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Published

2021-01-26

Issue

Vol. 57 No. 1 (2021)

Section

Original Papers