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

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 Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2022, Volume: 27, Number: 19, Article number : 6287, Pages count : DOI: 10.3390/molecules27196287

Authors

Voronin Alexey A. ¹ , Balabanova Sofya P. ¹ , Fedyanin Ivan V. ² , Churakov Aleksandr M. ¹ , Pivkina Alla N. ³ , Strelenko Yurii A. ¹ , Klenov Michael S. ¹ , Tartakovsky Vladimir A. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russia
2	A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., 119991 Moscow, Russia
3	N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Building 1, 119991 Moscow, Russia

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.

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. V.27. N19. 6287 . DOI: 10.3390/molecules27196287 WOS Scopus OpenAlex

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