Anions Containing Tripoid Conjugated N(4)(−) 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

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; CH(2)CH(2)CN; NO(2) (4a); CN (4b); CO(2)Et (4c)) starting from 3-amino-4-azido-1,2,5-oxadiazole was developed. The key step in this strategy is the intramolecular thermolytic cycliz...

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Autores principales: Voronin, Alexey A., Balabanova, Sofya P., Fedyanin, Ivan V., Churakov, Aleksandr M., Pivkina, Alla N., Strelenko, Yurii A., Klenov, Michael S., Tartakovsky, Vladimir A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571959/
https://www.ncbi.nlm.nih.gov/pubmed/36234825
http://dx.doi.org/10.3390/molecules27196287
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author Voronin, Alexey A.
Balabanova, Sofya P.
Fedyanin, Ivan V.
Churakov, Aleksandr M.
Pivkina, Alla N.
Strelenko, Yurii A.
Klenov, Michael S.
Tartakovsky, Vladimir A.
author_facet Voronin, Alexey A.
Balabanova, Sofya P.
Fedyanin, Ivan V.
Churakov, Aleksandr M.
Pivkina, Alla N.
Strelenko, Yurii A.
Klenov, Michael S.
Tartakovsky, Vladimir A.
author_sort Voronin, Alexey A.
collection PubMed
description 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; CH(2)CH(2)CN; NO(2) (4a); CN (4b); CO(2)Et (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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spelling pubmed-95719592022-10-17 Anions Containing Tripoid Conjugated N(4)(−) 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 Voronin, Alexey A. Balabanova, Sofya P. Fedyanin, Ivan V. Churakov, Aleksandr M. Pivkina, Alla N. Strelenko, Yurii A. Klenov, Michael S. Tartakovsky, Vladimir A. Molecules Article 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; CH(2)CH(2)CN; NO(2) (4a); CN (4b); CO(2)Et (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. MDPI 2022-09-23 /pmc/articles/PMC9571959/ /pubmed/36234825 http://dx.doi.org/10.3390/molecules27196287 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Voronin, Alexey A.
Balabanova, Sofya P.
Fedyanin, Ivan V.
Churakov, Aleksandr M.
Pivkina, Alla N.
Strelenko, Yurii A.
Klenov, Michael S.
Tartakovsky, Vladimir A.
Anions Containing Tripoid Conjugated N(4)(−) 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
title Anions Containing Tripoid Conjugated N(4)(−) 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
title_full Anions Containing Tripoid Conjugated N(4)(−) 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
title_fullStr Anions Containing Tripoid Conjugated N(4)(−) 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
title_full_unstemmed Anions Containing Tripoid Conjugated N(4)(−) 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
title_short Anions Containing Tripoid Conjugated N(4)(−) 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
title_sort anions containing tripoid conjugated n(4)(−) 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571959/
https://www.ncbi.nlm.nih.gov/pubmed/36234825
http://dx.doi.org/10.3390/molecules27196287
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