Reaction of 2-methylene-1,3-dicarbonyl compounds containing a CF3-group with 1,3-dienes

Valentine G. Nenajdenko, Alexander V. Statsuk, Elizabeth S. Balenkova

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

The Knoevenagel condensation of 1-substituted 4,4,4-trifluorobutan-1,3-diones with paraformaldehyde in the presence of cyclic and linear 1,3-dienes leads to Diels-Alder cycloadducts via in situ formation of the appropriate 2-methylene-1,3-dicarbonyl compounds 2(a-c). In the reactions with linear 1,3-dienes, compounds 2(a-c) react as dienophiles. In the case of the reactions with cyclic 1,3-dienes both normal and inverse demand Diels-Alder reactions take place.

Original languageEnglish (US)
Pages (from-to)6549-6556
Number of pages8
JournalTetrahedron
Volume56
Issue number35
DOIs
StatePublished - Aug 25 2000

Keywords

  • 2-methylene-1,3-dicarbonyl compounds
  • Diels-Alder reaction
  • Hetero-dienes
  • Trifluoromethyl ketones
  • α,β-unsaturated ketones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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