<i>S</i><sub>N</sub><sup>H</sup> ALKYL CARBAMOYL AMINATION OF 3-NITROPYRIDINE: COMPETITIVE SYNTHESIS OF NITRO- AND NITROSOPYRIDINE DERIVATIVES

Authors

  • Елена К. Авакян North Caucasus Federal University, 1a Pushkina St., Stavropol 355009
  • Иван В. Боровлев North Caucasus Federal University, 1a Pushkina St., Stavropol 355009
  • Олег П. Демидов North Caucasus Federal University, 1a Pushkina St., Stavropol 355009
  • Гульминат А. Амангазиева North Caucasus Federal University, 1a Pushkina St., Stavropol 355009
  • Диана Ю. Побединская North Caucasus Federal University, 1a Pushkina St., Stavropol 355009

DOI:

https://doi.org/10.1007/4163

Keywords:

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

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

Author Biographies

Елена К. Авакян, North Caucasus Federal University, 1a Pushkina St., Stavropol 355009

Кафедра химии

Иван В. Боровлев, North Caucasus Federal University, 1a Pushkina St., Stavropol 355009

Кафедра химии

Олег П. Демидов, North Caucasus Federal University, 1a Pushkina St., Stavropol 355009

Кафедра химии

Диана Ю. Побединская, North Caucasus Federal University, 1a Pushkina St., Stavropol 355009

Кафедра химии

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Published

2017-12-21

Issue

Vol. 53 No. 11 (2017)

Section

Original Papers