6-HYDROXYAURONE AMINOMETHYL DERIVATIVES IN THE INVERSE ELECTRON-DEMAND DIELS–ALDER REACTION

Authors

  • Антонина В. Попова V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kyiv 02094
  • Галина П. Мруг V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kyiv 02094
  • Cветлана Петровна Бондаренко National University of Food Technologies, 68 Volodymyrska St., Kyiv 01601
  • Михаил С. Фрасинюк V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kyiv 02094

DOI:

https://doi.org/10.1007/5152

Keywords:

aurone, enamine, Mannich base, o-quinone methide, vinyl ether, Diels–Alder reaction

Abstract

The transformations of 7-dimethylaminomethyl-6-hydroxyaurone and 5-dimethylaminomethyl-6-hydroxy-7-methylurone in the inversed electron-demand hetero-Diels–Alder reaction were studied. As a result of in situ thermal formation of o-quinone methides containing the benzofuranone moiety and cycloaddition of cyclic vinyl esters, 2-benzylidene derivatives of difuro[2,3-b:2',3'-f]chromen-3(2H)-one, furo[2,3-f]pyrano[2,3-b]chromen-3(2H)-one, difuro[2,3-b:3',2'-g]chromen-3(2H)-one, and furo[3,2-g]pyrano[2,3-b]chromen-3(2H)-one heterocyclic systems were synthesized. A similar reaction with cyclic enamines, accompanied by subsequent transformation of hemiaminals, led to the formation of partially hydrogenated derivatives of furo[2,3-a]xanthen-3(2H)-one and furo[3,2-b]xanthen-3(2H)-one.

Authors: Antonina V. Popova, Galyna P. Mrug, Svitlana P. Bondarenko, Mikhaylo S. Frasinyuk*

Published

2019-12-18

Issue

Section

Original Papers