Abstract
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 COCF 3 group—vinylog of sulfonylurea 6a and tosylamide 7a , correspondingly.
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