Regioselective reactions of N-monosubstituted β-aminovinyl trifluoromethyl ketones with tosyl isocyanate

The NH and α-CH insertion reactions of tosyl isocyanate with N-monosubstituted 4-amino-1,1,1-trifluorobut-3-en-2-ones have been studied. The regioselectivity of this reaction depends on the temperature, the nature of the solvent and the catalyst: high temperatures or basic catalysts direct in favour...

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Bibliographic Details
Published in:Tetrahedron letters 2000-12, Vol.41 (51), p.10141-10145
Main Authors: Gerus, Igor I, Lyutenko, Natalie V, Kacharov, Alexey D, Kukhar, Valery P
Format: Article
Language:English
Subjects:
enaminones
insertion reactions
regiochemistry
tosyl isocyanate
ureas
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Summary:The NH and α-CH insertion reactions of tosyl isocyanate with N-monosubstituted 4-amino-1,1,1-trifluorobut-3-en-2-ones have been studied. The regioselectivity of this reaction depends on the temperature, the nature of the solvent and the catalyst: high temperatures or basic catalysts direct in favour of NH insertion while low temperatures direct the process in favour of α-CH insertion.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)01804-9