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

Olga Yur'evna Ozerova 1
Olga Yur'evna Ozerova
, 
Tatiana Petrovna Efimova 1
Tatiana Petrovna Efimova
, 
Tamara Aleksandrovna Novikova 1
Tamara Aleksandrovna Novikova
, 
Igor Anatol'evich Litvinov 2
Igor Anatol'evich Litvinov
, 
Sergey Valentinovich Makarenko 1
Sergey Valentinovich Makarenko
1 Herzen State Pedagogical University of Russia, St. Petersburg, Russian Federation
2 A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
10.1016/j.mencom.2024.02.033
Published 2024-02-19
Communication , Volume 34, Issue 2, 265-267
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Ozerova O. Y. et al. Reactions of 1-amino-2-nitroguanidine with 3-nitroacrylates // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 265-267.
GOST all authors (up to 50) Copy
Ozerova O. Y., Efimova T. P., Novikova T. A., Litvinov I. A., Makarenko S. V. Reactions of 1-amino-2-nitroguanidine with 3-nitroacrylates // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 265-267.
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TY - JOUR
DO - 10.1016/j.mencom.2024.02.033
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.033
TI - Reactions of 1-amino-2-nitroguanidine with 3-nitroacrylates
T2 - Mendeleev Communications
AU - Ozerova, Olga Yur'evna
AU - Efimova, Tatiana Petrovna
AU - Novikova, Tamara Aleksandrovna
AU - Litvinov, Igor Anatol'evich
AU - Makarenko, Sergey Valentinovich
PY - 2024
DA - 2024/02/19
PB - Mendeleev Communications
SP - 265-267
IS - 2
VL - 34
ER -
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@article{2024_Ozerova,
author = {Olga Yur'evna Ozerova and Tatiana Petrovna Efimova and Tamara Aleksandrovna Novikova and Igor Anatol'evich Litvinov and Sergey Valentinovich Makarenko},
title = {Reactions of 1-amino-2-nitroguanidine with 3-nitroacrylates},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.033},
number = {2},
pages = {265--267},
doi = {10.1016/j.mencom.2024.02.033}
}
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Ozerova, Olga Yur'evna, et al. “Reactions of 1-amino-2-nitroguanidine with 3-nitroacrylates.” Mendeleev Communications, vol. 34, no. 2, Feb. 2024, pp. 265-267. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.033.

Keywords

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

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.

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