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SNH ALKYL CARBAMOYL AMINATION OF 3-NITROPYRIDINE: COMPETITIVE SYNTHESIS OF NITRO- AND NITROSOPYRIDINE DERIVATIVES

Елена К. Авакян, Иван В. Боровлев, Олег П. Демидов, Гульминат А. Амангазиева, Диана Ю. Побединская
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Abstract


A method has been developed for oxidative SNH 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.

Authors: Elena K. Avakyan, Ivan V. Borovlev*, Oleg P. Demidov, Gulminat A. Amangasieva, Diana Yu. Pobedinskaya


Keywords


3-nitropyridine; ureas; SNH alkyl carbamoyl amination; SNH methodology

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