Sciact
  • EN
  • RU

R-substituent vs exocyclic oxygen: influence on synthesis and crystal packing of R-[1,2,5]oxadiazolo[3,4-c]cinnoline mono- and dioxides Научная публикация

Журнал CrystEngComm
ISSN: 1466-8033
Вых. Данные Год: 2025, Том: 27, Номер: 3, Страницы: 372-385 Страниц : 14 DOI: 10.1039/d4ce01068j
Авторы Zelenov Victor P. 1 , Fedyanin Ivan V. 2,3 , Samigullina Aida I. 1 , Larin Alexandr A. 1,3 , Sheremetev Aleksei B. 1
Организации
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russian Federation
2 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., 119991, Moscow, Russian Federation
3 National Research University Higher School of Economics, 20 Myasnitskaya St., 101000 Moscow, Russian Federation

Реферат: A series of R-[1,2,5]oxadiazolo[3,4-c]cinnoline 5-mono- and 1,5-dioxides containing substituents (R = CH3, F, Br, CF3) at different positions were synthesized by an N-nitration–annulation process occurring upon treatment of 3-amino-4-(R-aryl)furazans and 4-amino-3-(R-aryl)furoxans with the HNO3–H2SO4–Ac2O system. The regioselectivity of the ring closure step was determined for the unsymmetrically substituted R-aryl precursors. Unexpected acylation at position 6 of 7-bromo-[1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxide occurred as a result of the increased duration of the synthesis. The crystal structures of five new compounds were determined by X-ray diffraction analysis, and their crystal packings were compared with each other and with those of previously studied molecules, revealing common motifs regardless of the type or position of the substituent. Specifically, the fluorine derivative forms layers isostructural with those in unsubstituted mono- and dioxides, differing only in their arrangement within the P21 and P21/c space groups. Two methyl derivatives, on the other hand, exhibit a structure with flat layers. While the crystal environments of different R-substituents are generally distinct, the unsubstituted part of the heterocyclic core tends to form repeating isostructural motifs, such as dimers, chains, and layers. Although substituents disrupt the crystal packing, they still allow for the combination of these motifs in different crystal structures.
Библиографическая ссылка: Zelenov V.P. , Fedyanin I.V. , Samigullina A.I. , Larin A.A. , Sheremetev A.B.
R-substituent vs exocyclic oxygen: influence on synthesis and crystal packing of R-[1,2,5]oxadiazolo[3,4-c]cinnoline mono- and dioxides
CrystEngComm. 2025. V.27. N3. P.372-385. DOI: 10.1039/d4ce01068j WOS OpenAlex
Идентификаторы БД:
Web of science: WOS:001374887200001
OpenAlex: W4404998106
Цитирование в БД: Пока нет цитирований
Альметрики: