INVERSE ELECTRON DEMAND DIELS–ALDER REACTIONS WITH AMINOMETHYL DERIVATIVES OF 3-ARYLHYDROXYCOUMARINS

Authors

  • Галина П. Мруг Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kiyv 02094
  • Константин М. Кондратюк Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kiyv 02094
  • Светлана П. Бондаренко National Institute of Food Technologies, 68 Volodymyrska St., Kiyv 01601
  • Михаил С. Фрасинюк Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kiyv 02094

DOI:

https://doi.org/10.1007/3222

Keywords:

coumarin, enamine, Mannich base, o-quinone methid, Diels–Alder reaction

Abstract

The reactivity of Mannich bases derived from 6- and 7-hydroxycoumarins was studied in inverse electron demand Diels–Alder reactions with enamines. The reactions were shown to proceed by a cycloaddition mechanism followed by transformation of hemiaminals and resulted in the formation of heterocyclic pyrano[2,3-a]xanthene, pyrano[2,3-b]xanthene, and pyrano[3,2-b]xanthene.

Authors: Galyna P. Mrug, Kostyantyn M. Kondratyuk,
Svitlana P. Bondarenko, Mykhaylo S. Frasinyuk*

Author Biographies

Галина П. Мруг, Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kiyv 02094

Галина Петровна Мруг

Константин М. Кондратюк, Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kiyv 02094

Константин Михайлович Кондратюк

Светлана П. Бондаренко, National Institute of Food Technologies, 68 Volodymyrska St., Kiyv 01601

Светлана Петровна Бондаренко

Михаил С. Фрасинюк, Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kiyv 02094

Михаил Сергеевич Фрасинюк

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Published

2016-07-18

Issue

Vol. 52 No. 7 (2016)

Section

Original Papers