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Regioselective quaternization of N-alkyl-4-nitro- 1,2,3-triazoles in ButOH–HClO4 system

Gennady Timofeevich Sukhanov 1
Gennady Timofeevich Sukhanov
Gennady Viktorovich Sakovich 1
Gennady Viktorovich Sakovich
Yulia Vadimovna Filippova 1
Yulia Vadimovna Filippova
Irina Yur'evna Bagryanskaya 2, 3
Irina Yur'evna Bagryanskaya
Anna Gennadievna Sukhanova 1
Anna Gennadievna Sukhanova
Published 2014-09-04
CommunicationVolume 24, Issue 5, 280-282
5
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Sukhanov G. T. et al. Regioselective quaternization of N-alkyl-4-nitro- 1,2,3-triazoles in ButOH–HClO4 system // Mendeleev Communications. 2014. Vol. 24. No. 5. pp. 280-282.
GOST all authors (up to 50) Copy
Sukhanov G. T., Sakovich G. V., Filippova Y. V., Bagryanskaya I. Y., Sukhanova A. G. Regioselective quaternization of N-alkyl-4-nitro- 1,2,3-triazoles in ButOH–HClO4 system // Mendeleev Communications. 2014. Vol. 24. No. 5. pp. 280-282.
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TY - JOUR
DO - 10.1016/j.mencom.2014.09.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.09.011
TI - Regioselective quaternization of N-alkyl-4-nitro- 1,2,3-triazoles in ButOH–HClO4 system
T2 - Mendeleev Communications
AU - Sukhanov, Gennady Timofeevich
AU - Sakovich, Gennady Viktorovich
AU - Filippova, Yulia Vadimovna
AU - Bagryanskaya, Irina Yur'evna
AU - Sukhanova, Anna Gennadievna
PY - 2014
DA - 2014/09/04
PB - Mendeleev Communications
SP - 280-282
IS - 5
VL - 24
ER -
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@article{2014_Sukhanov,
author = {Gennady Timofeevich Sukhanov and Gennady Viktorovich Sakovich and Yulia Vadimovna Filippova and Irina Yur'evna Bagryanskaya and Anna Gennadievna Sukhanova},
title = {Regioselective quaternization of N-alkyl-4-nitro- 1,2,3-triazoles in ButOH–HClO4 system},
journal = {Mendeleev Communications},
year = {2014},
volume = {24},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.09.011},
number = {5},
pages = {280--282},
doi = {10.1016/j.mencom.2014.09.011}
}
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Cite this
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Sukhanov, Gennady Timofeevich, et al. “Regioselective quaternization of N-alkyl-4-nitro- 1,2,3-triazoles in ButOH–HClO4 system.” Mendeleev Communications, vol. 24, no. 5, Sep. 2014, pp. 280-282. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.09.011.

Abstract

Quaternization of N-alkyl-4-nitro-1,2,3-triazoles in ButOH–HClO4 as a source of tert-butyl cation affords 1-tert-butyl-3-alkyl-4-nitro- 1,2,3-triazolium perchlorates.

References

1.
Antiplatelet properties of novel N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone derivatives
Cunha A.C., Figueiredo J.M., Tributino J.L., Miranda A.L., Castro H.C., Zingali R.B., Fraga C.A., de Souza M.C., Ferreira V.F., Barreiro E.J.
Bioorganic and Medicinal Chemistry, 2003
2.
Synthesis and antibacterial activity of 5-substituted oxazolidinones
Phillips O.A., Udo E.E., Ali A.A., Al-Hassawi N.
Bioorganic and Medicinal Chemistry, 2003
3.
N. D. Cosford and L. R. Tehrani, Patent PCT Int. Appl. WO 03/051315 A2, A61K, 2003 (Chem. Abstr., 2003, 139, 69268).
4.
Cell Surface Labeling of Escherichia coli via Copper(I)-Catalyzed [3+2] Cycloaddition
Link A.J., Tirrell D.A.
Journal of the American Chemical Society, 2003
5.
W.-Q. Fan and A. R. Katritzky, in Comprehensive Heterocyclic Chemistry II, eds. A. R. Katritzky, C.W. Rees and E. F. V. Scriven, Elsevier Science, Oxford, 1996, vol. 4, p. 126.
6.
New energetic materials from triazoles and tetrazines
Licht H., Ritter H.
Journal of Energetic Materials, 1994
7.
Synthesis and Explosive Properties of Dinitrobitriazole
Licht H.H., Ritter H.
Propellants, Explosives, Pyrotechnics, 1997
8.
Ionic Liquids Based on Azolate Anions
Smiglak M., Hines C. ., Wilson T., Singh S., Vincek A., Kirichenko K., Katritzky A., Rogers R.
Chemistry - A European Journal, 2010
9.
Energetic, Low-Melting Salts of Simple Heterocycles
Drake G., Hawkins T., Brand A., Hall L., Mckay M., Vij A., Ismail I.
Propellants, Explosives, Pyrotechnics, 2003
10.
N-Alkylation of 4-nitro-1,2,3-triazole revisited. Detection and characterization of the N3-ethylation product, 1-ethyl-5-nitro-1,2,3-triazole
Voitekhovich S.V., Gaponik P.N., Lyakhov A.S., Filipova J.V., Sukhanova A.G., Sukhanov G.T., Ivashkevich O.A.
Tetrahedron Letters, 2009
11.
Selective complexation of 1-ethyl-5-nitro-1,2,3-triazole (entz) with copper(II) salts: Preparation and characterization of [Cu(entz)2Cl2] and [Cu(entz)4(H2O)2](ClO4)2
Voitekhovich S.V., Filippova J.V., Sukhanova A.G., Lyakhov A.S., Ivashkevich L.S., Sukhanov G.T., Grigoriev Y.V.
Inorganic Chemistry Communication, 2012
12.
Acid Catalyzedtert-Butylation and Tritylation of 4-Nitro-1,2,3-triazole: Selective Synthesis of 1-Methyl-5-nitro-1,2,3-triazole via 1-tert-Butyl-4-nitro-1,2,3-triazole
Filippova Y.V., Sukhanova A.G., Voitekhovich S.V., Matulis V.E., Sukhanov G.T., Grigoriev Y.V., Ivashkevich O.A.
Journal of Heterocyclic Chemistry, 2012
13.
O. A. Ivashkevich, Vad. E. Matulis, P.N. Gaponik, G.T. Sukhanov, J. V. Filippova and A. G. Sukhanova, Chem. Heterocycl. Compd. (Engl. Transl.), 2008, 44, 1472 (Khim. Geterotsikl. Soedin., 2008, 1816).
14.
Alkylation of 4(5)-nitro-1,2,3-triazole with alcohols in strongly acidic media
Sakovich G.V., Sukhanov G.T., Filippova Y.V., Sukhanova A.G., Bosov K.K.
Russian Chemical Bulletin, 2013
15.
Reactions of 4-nitro-1,2,3-triazole with alkylating agents and compounds with activated multiple bonds
Vereshchagin L.I., Kuznetsova N.I., Kirillova L.P., Shcherbakov V.V., Sukhanov G.T., Gareev G.A.
Chemistry of Heterocyclic Compounds, 1986
16.
O. A. Ivashkevich, Vad. E. Matulis, A.S. Lyakhov, I.N. Grigorieva, P.N. Gaponik, G.T. Sukhanov, Yu. V. Filippova and A. G. Sukhanova, Chem. Heterocycl. Compd. (Engl. Transl.), 2009, 45, 1218 (Khim. Geterotsikl. Soedin., 2009, 1519).
17.
Adamantylazoles. Acid-catalyzed adamantylation of 1,2,4-triazoles
Saraev V.V., Kanakina T.P., Pevzner M.S., Golod E.L., Ugrak B.I., Kachala V.V.
Chemistry of Heterocyclic Compounds, 1996
18.
10.1016/j.mencom.2014.09.011_sbref0045a
Trofimov
Zh. Org. Khim., 1995
19.
Basicity of N-H- and N-Methyl-1,2,3-triazoles in the Gas Phase, in Solution, and in the Solid State − An Experimental and Theoretical Study
Abboud J., Foces-Foces C., Notario R., Trifonov R., Volovodenko A., Ostrovskii V., Alkorta I., Elguero J.
European Journal of Organic Chemistry, 2001
20.
Acid‐mediated regioselective alkylation of 1,2,3‐triazole
21.
G. M. Sheldrick, SHELX-97, Programs for Crystal Structure Analysis (Release 97-2), University of Göttingen, Germany, 1997.
22.
SADABS, v. 2008-1, Bruker AXS, Madison, WI, USA, 2008.