[1,2,5]Oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides: Efficient Synthesis via the Reaction of 3,4-bis(Hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxides with a Mixture of Concentrated Nitric and Trifluoroacetic Acids and Structural Characterization Научная публикация
Журнал |
Tetrahedron Letters
ISSN: 0040-4039 |
||||||
---|---|---|---|---|---|---|---|
Вых. Данные | Год: 2018, Том: 59, Номер: 32, Страницы: 3143-3146 Страниц : 4 DOI: 10.1016/j.tetlet.2018.07.015 | ||||||
Ключевые слова | [1,2,5]Oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides; 3,4-Bis(hydroxyimino)methyl)-1,2,5- oxadiazole 2-oxides; Nitric acid; Intermolecular interactions; Synchrotron X-ray diffraction | ||||||
Авторы |
|
||||||
Организации |
|
Реферат:
An efficient synthesis of [1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides (1) from
3,4-bis(hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxides using a mixture of concentrated nitric and trifluoroacetic acids has been developed. The scope of the unconventional reaction was established. The 4,7-dinitro[1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide
1f represents a new high energy compound, unfortunately with low thermal stability. The parent [1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide 1c was studied by single-crystal
X-ray diffraction analysis which revealed a planar molecule with an unusually long intracyclic N-N bond of 1.668(5) Å and unexpected exo-cyclic bond angles at the nitroxyl nitrogen atoms. In the crystal, the molecules of 1c are bound to each other by strong π-π stacking and C-H⋯O hydrogen bonding interactions into a three-dimensional framework that results in a high crystal density of 1.833 gcm−3.
Библиографическая ссылка:
Ogurtsov V.A.
, Dorovatovskii P.V.
, Zubavichus Y.V.
, Khrustalev V.N.
, Fakhrutdinov A.N.
, Zlotin S.G.
, Rakitin O.A.
[1,2,5]Oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides: Efficient Synthesis via the Reaction of 3,4-bis(Hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxides with a Mixture of Concentrated Nitric and Trifluoroacetic Acids and Structural Characterization
Tetrahedron Letters. 2018. V.59. N32. P.3143-3146. DOI: 10.1016/j.tetlet.2018.07.015 WOS Scopus РИНЦ
[1,2,5]Oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides: Efficient Synthesis via the Reaction of 3,4-bis(Hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxides with a Mixture of Concentrated Nitric and Trifluoroacetic Acids and Structural Characterization
Tetrahedron Letters. 2018. V.59. N32. P.3143-3146. DOI: 10.1016/j.tetlet.2018.07.015 WOS Scopus РИНЦ
Даты:
Поступила в редакцию: | 28 мая 2018 г. |
Принята к публикации: | 3 июл. 2018 г. |
Опубликована online: | 4 июл. 2018 г. |
Опубликована в печати: | 8 авг. 2018 г. |
Идентификаторы БД:
Web of science | WOS:000440123000021 |
Scopus | 2-s2.0-85049579854 |
РИНЦ | 35774741 |
Chemical Abstracts | 2018:1288092 |
Chemical Abstracts (print) | 169:265501 |
OpenAlex | W2811303230 |