Open Access
Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability
Alexey A Voronin
1
,
Ivan V. Fedyanin
2
,
Alla N Pivkina
3
,
Yurii A. Strelenko
1
,
Michael S Klenov
1
,
Vladimir A Tartakovsky
1
Publication type: Journal Article
Publication date: 2022-09-23
PubMed ID:
36234825
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
A strategy for the synthesis of 5-((2-cyanoethyl)-X-amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides (X = H; CH2CH2CN; NO2 (4a); CN (4b); CO2Et (4c)) starting from 3-amino-4-azido-1,2,5-oxadiazole was developed. The key step in this strategy is the intramolecular thermolytic cyclization of the azido group and the bis(2-cyanoethyl)triazene group. Removal of the 2-cyanoethyl protecting group from amides 4a–c gave potassium salt of the corresponding nitramide and sodium salts of cyano- and ethoxycarbonylamide. The structure and thermal stability of the synthesized compounds were studied experimentally using multinuclear NMR spectroscopy, X-ray crystallography, thermogravimetry, and differential scanning calorimetry.
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11
Total citations:
11
Citations from 2025:
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(18.18%)
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Voronin A. A. et al. Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability // Molecules. 2022. Vol. 27. No. 19. p. 6287.
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Voronin A. A., Balabanova S. P., Fedyanin I. V., Churakov A. M., Pivkina A. N., Strelenko Y. A., Klenov M. S., Tartakovsky V. A. Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability // Molecules. 2022. Vol. 27. No. 19. p. 6287.
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RIS
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TY - JOUR
DO - 10.3390/molecules27196287
UR - https://doi.org/10.3390/molecules27196287
TI - Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability
T2 - Molecules
AU - Voronin, Alexey A
AU - Balabanova, Sofya P
AU - Fedyanin, Ivan V.
AU - Churakov, Aleksandr M
AU - Pivkina, Alla N
AU - Strelenko, Yurii A.
AU - Klenov, Michael S
AU - Tartakovsky, Vladimir A
PY - 2022
DA - 2022/09/23
PB - MDPI
SP - 6287
IS - 19
VL - 27
PMID - 36234825
SN - 1420-3049
ER -
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BibTex (up to 50 authors)
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@article{2022_Voronin,
author = {Alexey A Voronin and Sofya P Balabanova and Ivan V. Fedyanin and Aleksandr M Churakov and Alla N Pivkina and Yurii A. Strelenko and Michael S Klenov and Vladimir A Tartakovsky},
title = {Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability},
journal = {Molecules},
year = {2022},
volume = {27},
publisher = {MDPI},
month = {sep},
url = {https://doi.org/10.3390/molecules27196287},
number = {19},
pages = {6287},
doi = {10.3390/molecules27196287}
}
Cite this
MLA
Copy
Voronin, Alexey A., et al. “Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability.” Molecules, vol. 27, no. 19, Sep. 2022, p. 6287. https://doi.org/10.3390/molecules27196287.