Reactivity of chloroacetylated β-enamino compounds. Synthesis of heterocycles

Ethyl (E)-(3-amino substituted)-2-chloroacetyl-2-butenoates 2c–g, N-[(Z)-1-methyl-3-oxo-1-butenyl]-2-chloroacetamide 3a and ethyl (Z)-3-chloromethyl carboxamino-2-butenoate 3c, have been prepared from β-amino α,β-unsaturated ketone 1a and esters 1c–g and chloroacetyl chloride. The reactivity of these compounds was studied by the reactions with binucleophiles, such as hydrazine and hydroxylamine, to evaluate the electrophilic centers in the formation of the polyfunctionalized heterocyclic compounds.