Anions Containing Tripoid Conjugated N[sub.4][sup.−] System: Salts of 5--[1,2,3]triazolo[4,5-Ic/I][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 19
• Main Authors: Voronin, Alexey A, Balabanova, Sofya P, Fedyanin, Ivan V, Churakov, Aleksandr M, Pivkina, Alla N, Strelenko, Yurii A, Klenov, Michael S, Tartakovsky, Vladimir A
• Format: Journal Article
• Language: English
• Published: MDPI AG 01-09-2022
• Subjects: Nitrates; Nitrogen; Nuclear magnetic resonance spectroscopy
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27196287

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[sub.2]CH[sub.2]CN; NO[sub.2] (4a); CN (4b); CO[sub.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.