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Synthesis and Physicochemical Properties of Energetic 1,2,4,5‐Tetrazinyl Derivatives of 5‐Nitro‐2,4‐dihydro‐1,2,4‐triazol‐3‐oneстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 29 сентября 2021 г.
- Авторы: Rudakov Gennady F., Kozlov Ivan B., Boev Nikolay V., Zinchenko Svetlana S., Melnikova Lyudmila Ya, Egorshev Viacheslav Yu, Sinditskii Valery P.
- Журнал: ChemistrySelect
- Том: 6
- Номер: 30
- Год издания: 2021
- Первая страница: 7654
- Последняя страница: 7662
- DOI: 10.1002/slct.202102160
- Аннотация: By replacing the pyrazolyl fragment in 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine with 3-nitro-1,2,4-triazol-5-one (NTO), both mono- and disubstitution products have been synthesized. Further interaction of the obtained compounds with O- and N-nucleophiles led to the preparation of a number of polynitrogen tetrazine derivatives, including 2-[6-amino-1,2,4,5-tetrazin-3-yl]-5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one and 5-nitro-2- [6-(1H-tetrazol-5-ylamino)-1,2,4,5-tetrazine-3-yl]-2,4-dihydro-3H-1,2,4-triazol-3-one. The reactions of nucleophilic substitution of symmetrically substituted tetrazine were shown to proceed more selectively. The resulting compounds were identified using 1H, 13CNMR spectroscopy, FTIR, LC-MS, and elemental analysis, as well as using X-ray diffraction analysis. The thermal stability of the new compounds was evaluated under isothermal and non-isothermal conditions and their energy characteristics were calculated. An unusual drop in stability was found on going from symmetrically substituted tetrazines to asymmetric ones.
- Добавил в систему: Синдицкий Валерий Петрович