SNH Alkyl carbamoyl amination of 3-nitropyridine: competitive synthesis of nitro- and nitrosopyridine derivatives

Abstract

A method has been developed for oxidative SN H alkyl carbamoyl amination of 3-nitropyridine in anhydrous DMSO. When anions of alkyl- and 1,1-dialkylureas were used as nucleophiles, an unusual formation of a mixture consisting of 1-alkyl(1,1-dialkyl)-3-(5-nitropyridin-2-yl)ureas and their nitroso analogs occurred, which was the first such observation with 3-nitropyridine. Only the nitro products formed in the presence of nitrobenzene. Additionally, a range of N-oxides were obtained on the basis of the synthesized compounds