O. Yu. Ozerova, T. P. Efimova, T. A. Novikova, I. A. Litvinov, S. V. Makarenko, “Reactions of 1-amino-2-nitroguanidine with 3-nitroacrylates”, Mendeleev Commun., 2024, Volume 34, Issue 2,Pages <nobr>265

This article is cited in 1 paper

Communications

Reactions of 1-amino-2-nitroguanidine with 3-nitroacrylates

O. Yu. Ozerova^a, T. P. Efimova^a, T. A. Novikova^a, I. A. Litvinov^b, S. V. Makarenko^a

^a Herzen State Pedagogical University of Russia, St. Petersburg, Russian Federation
^b A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation

Abstract: The reactions of 1-amino-2-nitroguanidine with 3-nitro- acrylates afford aza-Michael adducts. The latter when refluxed in an aqueous alkaline medium undergo elimination of nitrous acid followed by shift of the resulting C=C bond into C=N position giving finally N-substituted alkylpyruvate hydrazones. These compounds can also be prepared in a one-pot procedure; NMR spectroscopy and X-ray diffraction analysis confirmed the existence of the obtained hydrazones as E-isomers.

Keywords: nitroguanidine, aminonitroguanidine, nitroacrylate, hydrazone, pyruvates, nucleophilic addition, aza-Michael adduct.

Language: English

DOI: 10.1016/j.mencom.2024.02.033

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