Fluoroalkylated α,β-Unsaturated Imines as Synthons for the Preparation of Fluorinated Triazinane-2,4-diones and Dihydropyrimidin-2(1H)‑ones

A regioselective addition of isocyanates to fluoroalkylated α,β-unsaturated imines 1 is described. Fluoroalkyl-substituted triazinane-2,4-diones 4 are obtained by the reaction of phenyl isocyanate with fluorinated imines 1, while fluorinated dihydropyridin-2(1H)-ones 7 are prepared when tosyl isocya...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-06, Vol.79 (11), p.5173-5181
Main Authors: Fernández de Trocóniz, Guillermo, Ochoa de Retana, Ana M, Rubiales, Gloria, Palacios, Francisco
Format: Article
Language:English
Subjects:
Catalysis
Halogenation
Imines - chemistry
Isocyanates - chemistry
Molecular Structure
Pyrimidinones - chemical synthesis
Pyrimidinones - chemistry
Stereoisomerism
Triazines - chemistry
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Summary:A regioselective addition of isocyanates to fluoroalkylated α,β-unsaturated imines 1 is described. Fluoroalkyl-substituted triazinane-2,4-diones 4 are obtained by the reaction of phenyl isocyanate with fluorinated imines 1, while fluorinated dihydropyridin-2(1H)-ones 7 are prepared when tosyl isocyanate is used. Tetrahydro-pyridin-2(1H)-one 10 is obtained by catalytic reduction of dihydropyridin-2(1H)-one 7. Computational studies are performed to explain the different behaviors of both isocyanates and the mechanisms of the processes.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500745u