3-Guanidino-6-R-1,2,4,5-tetrazines: azine ring transformation, nitration, and salt formation

The reaction of 3-azolyl-6-R-1,2,4,5-tetrazines with guanidine afforded a series of new 3-guanidino-6-R-1,2,4,5-tetrazines. When treated with hydrogen peroxide, these compounds can undergo oxidative transformation of the tetrazine ring to form 2,5-disubstituted 1,3,4-oxadiazoles. The reaction of the...

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Published inRussian chemical bulletin Vol. 72; no. 12; pp. 2965 - 2973
Main Authors Ishmetova, R. I., Ignatenko, N. K., Kuznetsova, E. A., Ganebnykh, I. N., Slepukhin, P. A., Gorbunov, E. B., Rusinov, G. L., Charushin, V. N.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.12.2023
Springer Nature B.V
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Functional groups
Hydrogen peroxide
Inorganic Chemistry
Nitration
Nitric acid
Organic Chemistry
guanidine
3,6-disubstituted 1,2,4,5-tetrazines
energetic salts
nucleophilic substitution
2,5-disubstituted 1,3,4-oxadiazoles
nitration
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Summary:The reaction of 3-azolyl-6-R-1,2,4,5-tetrazines with guanidine afforded a series of new 3-guanidino-6-R-1,2,4,5-tetrazines. When treated with hydrogen peroxide, these compounds can undergo oxidative transformation of the tetrazine ring to form 2,5-disubstituted 1,3,4-oxadiazoles. The reaction of the new tetrazines with concentrated nitric acid leads to the nitration of functional groups in the tetrazine ring.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-023-4107-4