Route to 1,2,4- and 1,2,5-oxadiazole ring assemblies via a one-pot condensation/oxidation protocol

Route to 1,2,4- and 1,2,5-oxadiazole ring assemblies via a one-pot condensation/oxidation protocol Научная публикация

Журнал

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Вых. Данные

Год: 2020, Том: 61, Номер: 13, Номер статьи : 151678, Страниц : DOI: 10.1016/j.tetlet.2020.151678

Авторы

Teslenko Fedor E. ^1,2 , Churakov Artem I. ² , Larin Alexander A. ² , Ananyev Ivan V. ^3,4 , Fershtat Leonid L. ² , Makhova Nina N. ²

Организации

1	Department of Chemistry, Moscow State University, 119991 Moscow, Leninskie Gory 1-3, Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prospect, 47, Moscow, Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilova str., 28, Moscow, Russia
4	National Research University Higher School of Economics, 101000, Vavilova str., 7, Moscow, Russian Federation

A novel one-pot approach for the synthesis of 1,2,4- and 1,2,5-oxadiazole ring assemblies has been developed. The synthetic strategy involves the condensation of furoxanyl amidoximes with aldehydes and subsequent iodine-mediated oxidation of the intermediate 1,2,4-oxadiazolines. The analogous reaction of 4-aminofuroxanyl-3-carboxamidoxime results not only in formation of the 1,2,4-oxadiazole subunit, but also rearrangement of the furoxan ring to the furazan one, which is the first example of a Lewis acid-promoted rearrangement in a furoxan series.

Teslenko F.E. , Churakov A.I. , Larin A.A. , Ananyev I.V. , Fershtat L.L. , Makhova N.N.
Route to 1,2,4- and 1,2,5-oxadiazole ring assemblies via a one-pot condensation/oxidation protocol
Tetrahedron Letters. 2020. V.61. N13. 151678 . DOI: 10.1016/j.tetlet.2020.151678 WOS Scopus OpenAlex

Web of science:	WOS:000527103500014
Scopus:	2-s2.0-85078738459
OpenAlex:	W3003861224

БД	Цитирований
OpenAlex	17
Scopus	18
Web of science	14