Volochnyuk D. Deactivated enamines as C-nucleophiles

New reaction of push-pull enamines bearing a–methyl group with methyl trifluoropyruvate, which runs at the methyl group of the enamines, was found. Also was found that the reaction of cyclocondensation of this enamines with hexafluoroacetylacetone and b-trifluoroacetylvinyl ethers leads to functionalized mono- and m-bis(trifluoromethyl)benzenes. A new approach to 5,6-dihydropyridin-2-ones comprising the reaction of the push-pull enamines with 1-chloroalkylisocyanates was elaborated. It was found that N-benzyl-3-cyano-1,4-dihydropyridine selectively enters into the electrophilic suibstitution reaction only with a limited set of highly active reagents such as EtO2CCOCl, p-MeC6H4SO2NCO, Vilsmeier-Haak’s reagent, sulphenyl chlorides and phosphorus tribromode.