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

doi:10.1016/S0040-4020(00)00605-0

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

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	6549-6556
Number of pages	8
Journal	Tetrahedron
Volume	56
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4020(00)00605-0
State	Published - 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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10.1016/S0040-4020(00)00605-0

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

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.",

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

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T1 - Reaction of 2-methylene-1,3-dicarbonyl compounds containing a CF3-group with 1,3-dienes

AU - Nenajdenko, Valentine G.

AU - Statsuk, Alexander V.

AU - Balenkova, Elizabeth S.

PY - 2000/8/25

Y1 - 2000/8/25

N2 - 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.

AB - 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.

KW - 2-methylene-1,3-dicarbonyl compounds

KW - Diels-Alder reaction

KW - Hetero-dienes

KW - Trifluoromethyl ketones

KW - α,β-unsaturated ketones

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