Kunihito Miyake

Amination of αβ-Unsaturated γ-Dicarbonyl Compounds with Methoxyamines

Abstract Methoxyamines were found to be efficient aminating agents for α,β-unsaturated γ-dicarbonyl compounds to give the corresponding α,β-diacyl enamines by a one-pot, two-step procedure.

A convenient copper-catalyzed direct amination of nitroarenes with O-alkylhydroxylamines

O-Alkylhydroxylamines, particularly O-methylhydroxylamine, aminate nitroarenes in the presence of a strong base and a copper catalyst to give aminonitroarenes in good yields. ortho- or para-Amination with respect to the nitro group takes place, and in some cases the ortho-aminated product is preferentially obtained. With 3-substituted nitrobenzenes where the substituent has a lone pair of electrons, preferential amination occurs at the 2-position to give the sterically most congested 3c–f, 14 and 22g.

Zinc-promoted direct amination of nitropyridines with methoxyamine via vicarious nucleophilic substitution

Direct amination of nitropyridines with methoxyamine in the presence of a stoichiometric amount of zinc(II) chloride under basic conditions proceeds to give aminonitropyridines.