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Nitration of 2,3-dihydroimidazo[1,2-a]benzimidazole and its N 9-substituted derivatives

Vadim Sergeevich Sochnev 1
Vadim Sergeevich Sochnev
, 
Tatyana Andreevna Kuz'menko 1
Tatyana Andreevna Kuz'menko
, 
Anatolii Savel'evich Morkovnik 1
Anatolii Savel'evich Morkovnik
, 
Lyudmila Nikolaevna Divaeva 1
Lyudmila Nikolaevna Divaeva
, 
Anastasia Sergeevna Podobina 1
Anastasia Sergeevna Podobina
, 
Alexander Aleksandrovich Zubenko 2
Alexander Aleksandrovich Zubenko
, 
Pavel Borisovich Chepurnoy 1
Pavel Borisovich Chepurnoy
, 
Gennadii Sergeevich Borodkin 1
Gennadii Sergeevich Borodkin
, 
Alexander Ivanovich Klimenko 2
Alexander Ivanovich Klimenko
2 North-Caucasian Zonal Research Veterinary Institute, Novocherkassk, Russian Federation
10.1016/j.mencom.2021.07.040
Published 2021-07-07
Communication , Volume 31, Issue 4, 555-557
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Sochnev V. S. et al. Nitration of 2,3-dihydroimidazo[1,2-a]benzimidazole and its N 9-substituted derivatives // Mendeleev Communications. 2021. Vol. 31. No. 4. pp. 555-557.
GOST all authors (up to 50) Copy
Sochnev V. S., Kuz'menko T. A., Morkovnik A. S., Divaeva L. N., Podobina A. S., Zubenko A. A., Chepurnoy P. B., Borodkin G. S., Klimenko A. I. Nitration of 2,3-dihydroimidazo[1,2-a]benzimidazole and its N 9-substituted derivatives // Mendeleev Communications. 2021. Vol. 31. No. 4. pp. 555-557.
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TY - JOUR
DO - 10.1016/j.mencom.2021.07.040
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.07.040
TI - Nitration of 2,3-dihydroimidazo[1,2-a]benzimidazole and its N 9-substituted derivatives
T2 - Mendeleev Communications
AU - Sochnev, Vadim Sergeevich
AU - Kuz'menko, Tatyana Andreevna
AU - Morkovnik, Anatolii Savel'evich
AU - Divaeva, Lyudmila Nikolaevna
AU - Podobina, Anastasia Sergeevna
AU - Zubenko, Alexander Aleksandrovich
AU - Chepurnoy, Pavel Borisovich
AU - Borodkin, Gennadii Sergeevich
AU - Klimenko, Alexander Ivanovich
PY - 2021
DA - 2021/07/07
PB - Mendeleev Communications
SP - 555-557
IS - 4
VL - 31
ER -
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@article{2021_Sochnev,
author = {Vadim Sergeevich Sochnev and Tatyana Andreevna Kuz'menko and Anatolii Savel'evich Morkovnik and Lyudmila Nikolaevna Divaeva and Anastasia Sergeevna Podobina and Alexander Aleksandrovich Zubenko and Pavel Borisovich Chepurnoy and Gennadii Sergeevich Borodkin and Alexander Ivanovich Klimenko},
title = {Nitration of 2,3-dihydroimidazo[1,2-a]benzimidazole and its N 9-substituted derivatives},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.07.040},
number = {4},
pages = {555--557},
doi = {10.1016/j.mencom.2021.07.040}
}
MLA
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Sochnev, Vadim Sergeevich, et al. “Nitration of 2,3-dihydroimidazo[1,2-a]benzimidazole and its N 9-substituted derivatives.” Mendeleev Communications, vol. 31, no. 4, Jul. 2021, pp. 555-557. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.07.040.

Abstract

7-Nitro-2,3-dihydroimidazo[1,2-a]benzimidazole and its N9-substituted derivatives can be conveniently synthesized by nitration of the corresponding tricyclic precursors with a nitrating mixture or with the HNO3 /CF3COOH system. This reaction occurs fairly smoothly and with good regioselectivity.

References

1.
V. A. Anisimova, I. E. Tolpygin, A. A. Spasov, V. A. Kosolapov, A. V. Stepanov and A. F. Kucheryavenko, Pharm. Chem. J., 2006, 40, 261 [Khim. Farm. Zh., 2006, 40 (5), 27].
2.
Synthesis and pharmacological activity of certain 2,3-dihydroimadazo[1,2-a]benzimidazoles and intermediates formed in their synthesis
Anisimova V.A., Levchenko M.V., Kovalev G.V., Spasov A.A., Dudchenko G.P., Antonyan S.G., Bessudnova N.V., Libinzon R.E.
Pharmaceutical Chemistry Journal, 1987
3.
10.1016/j.mencom.2021.07.040_b0015
Anisimova
Patent RU, 2010
4.
10.1016/j.mencom.2021.07.040_b0020
Spasov
Patent RU, 2012
5.
10.1016/j.mencom.2021.07.040_b0025
Dubua
Patent EA, 2010
6.
10.1016/j.mencom.2021.07.040_b0030
Anisimova
Patent EP, 1993
7.
Synthesis and pharmacological activity of amides of 2,3-dihydroimidazo- and 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazolyln-acetic acids
Anisimova V.A., Spasov A.A., Kosolapov V.A., Tolpygin I.E., Tibir’kova E.V., Salaznikova O.A., Kuznetsova V.A., Gurova N.A., Lenskaya K.V., Yakovlev D.S., Mal’tsev D.V., Kolobrodova N.A., Mitina T.M., Grechko O.Y.
Pharmaceutical Chemistry Journal, 2013
8.
Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a]benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi.
Oh S., Kim S., Kong S., Yang G., Lee N., Han D., Goo J., Siqueira-Neto J.L., Freitas-Junior L.H., Song R.
European Journal of Medicinal Chemistry, 2014
9.
6-Nitrobenzimidazole derivatives: Potential phosphodiesterase inhibitors: Synthesis and structure–activity relationship
Khan K.M., Shah Z., Ahmad V.U., Ambreen N., Khan M., Taha M., Rahim F., Noreen S., Perveen S., Choudhary M.I., Voelter W.
Bioorganic and Medicinal Chemistry, 2012
10.
10.1016/j.mencom.2021.07.040_b0050
Zhukovskaya
Patent RU, 2018
11.
V. A. Anisimova, M. V. Levchenko, Yu. V. Koschienko and A. F. Pozharskiy, Patent SU 952847, 1982.
12.
Research on benzimidazole.
Simonov A.M., Komissarov V.N.
Chemistry of Heterocyclic Compounds, 1975
13.
A study of some 1-alkyl-2,3-dihydroimidazo[1,2-a]benzimidazoles
North R.J., Day A.R.
Journal of Heterocyclic Chemistry, 1969
14.
V. A. Anisimova, I. E. Tolpygin and O. I. Askalepova, Chem. Heterocycl. Compd., 2014, 49, 1748 (Khim. Geterotsikl. Soedin., 2013, 1887).
15.
Synthesis and some conversions of N-substituted benzimidazole-2-sulfonic acids
Divaeva L.N., Kuzmenko T.A., Morkovnik A.S., Komissarov V.N.
Chemistry of Heterocyclic Compounds, 2006
17.
10.1016/j.mencom.2021.07.040_h0085
Kovalev
Patent RU, 1996
18.
10.1016/j.mencom.2021.07.040_h0090
Kreminskaya
Patent RU, 2013
19.
Nuclear Magnetic Resonance Shielding Tensors Calculated with a Sum-over-States Density Functional Perturbation Theory
Malkin V.G., Malkina O.L., Casida M.E., Salahub D.R.
Journal of the American Chemical Society, 1994