[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

[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 , E-ISSN: 1873-3581

Вых. Данные

Год: 2018, Том: 59, Номер: 32, Страницы: 3143-3146 Страниц : 4 DOI: 10.1016/j.tetlet.2018.07.015

Авторы

Ogurtsov Vladimir A. ¹ , Dorovatovskii Pavel V. ² , Zubavichus Yan V. ² , Khrustalev Victor N. ^2,3 , Fakhrutdinov Artem N. ¹ , Zlotin Sergei G. ¹ , Rakitin Oleg A. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia
2	National Research Center “Kurchatov Institute”, 123182 Moscow, Russia
3	Peoples’ Friendship University Russia (RUDN University), 117198 Moscow, Russia

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 Nsingle bondN 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 Csingle bondH⋯O hydrogen bonding interactions into a three-dimensional framework that results in a high crystal density of 1.833 gcm−3.

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 OpenAlex

Web of science:	WOS:000440123000021
Scopus:	2-s2.0-85049579854
OpenAlex:	W2811303230

БД	Цитирований
OpenAlex	17
Scopus	19
Web of science	15