Regioselective reactions of β-aminovinyl trifluoromethyl ketones with tosyl isocyanate

Natalie V. Lyutenko, Igor I. Gerus, Alexey D. Kacharov, Valery P. Kukhar

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


The NH- and α-CH-insertion reactions of tosyl isocyanate with N-monosubstituted and N,N-disubstituted trifluoromethyl-containing enaminones have been studied. The regioselectivity of N-tosylcarbomoylation of N-monosubstituted β-aminovinyl trifluoromethyl ketones depends on the structure of enaminones, the reaction temperature, the nature of solvent and catalyst. The Z configuration of fluorinated vinylogous sulphonylurea 3e was deduced from X-ray analysis. The reaction of N,N-disubstituted enaminone 5a with tosyl isocyanate gave the product mixture of electrophilic attack on either the α-CH- or the oxygen atom of COCF3 group - vinylog of sulfonylurea 6a and tosylamide 7a, correspondingly.

Original languageEnglish (US)
Pages (from-to)1731-1738
Number of pages8
Issue number10
StatePublished - Mar 3 2003
Externally publishedYes


  • Enaminones
  • N-tosylcarbomoylation
  • Polyfluoroalkyl ketones


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