Synthesis of Trifluoromethylpyrroles and Related Heterocycles from 4-Ethyloxy-1,1,1-trifluorobut-3-ene-2-one

Syntheses of intermediate 4-dialkylamino-1,1,1-trifluorobut-3-ene-2-ones are described from 4-ethyloxy-1,1,1-trifluorobut-3-ene-2-one and α-aminoacids. In subsequent cyclisations pyrroles and other bicyclic heteroaromatics having trifluoromethyl substitution are obtained either by simple dehydration...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 37; pp. 7267 - 7272
Main Authors Andrew, Rebecca J, Mellor, John M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.09.2000
Elsevier
Subjects
amino acids
Chemistry
Chemistry, Organic
Physical Sciences
pyrroles
Science & Technology
thiaproline
trifluoromethyl
trifluoromethyl
pyrroles
thiaproline
amino acids
NITROGEN-HETEROCYCLES
FLUORINE-CONTAINING 1,2-DIHYDROPYRIMIDINES
EFFICIENT SYNTHESIS
CONVENIENT
STRUCTURAL DETERMINATION
KETONES
FACILE SYNTHESIS
MAGNETIC-RESONANCE
CYCLIZATION
HALOACETYLATED ENOL ETHERS
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Summary:Syntheses of intermediate 4-dialkylamino-1,1,1-trifluorobut-3-ene-2-ones are described from 4-ethyloxy-1,1,1-trifluorobut-3-ene-2-one and α-aminoacids. In subsequent cyclisations pyrroles and other bicyclic heteroaromatics having trifluoromethyl substitution are obtained either by simple dehydration or with concomitant decarboxylation.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00598-6