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S N H Alkyl carbamoyl amination of 3-nitropyridine: competitive synthesis of nitro- and nitrosopyridine derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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This work received financial support from the Ministry of Education and Science of the Russian Federation within the framework of State Assignment (project No. 4.6306.2017/BCh).

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Authors and Affiliations

  1. North Caucasus Federal University, 1a Pushkina St., Stavropol, 355009, Russia

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

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  1. Elena K. Avakyan
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  2. Ivan V. Borovlev
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  3. Oleg P. Demidov
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  4. Gulminat A. Amangasieva
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  5. Diana Yu. Pobedinskaya
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Correspondence to Ivan V. Borovlev.

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The Supplementary information file containing 1Н and 13С NMR spectra of compounds 2a–g, 3a–g, 5b–d and IR spectra of compounds 2a–g, 5b–d is available at the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii,2017, 53(11), 1207–1213

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Avakyan, E.K., Borovlev, I.V., Demidov, O.P. et al. S N H Alkyl carbamoyl amination of 3-nitropyridine: competitive synthesis of nitro- and nitrosopyridine derivatives. Chem Heterocycl Comp 53, 1207–1213 (2017). https://doi.org/10.1007/s10593-018-2201-6

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  • DOI: https://doi.org/10.1007/s10593-018-2201-6

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