Deoxygenative Arylation of 5,6-Dihydro-4H-1,2-oxazine-N-oxides with Arynes | Sciact

Deoxygenative Arylation of 5,6-Dihydro-4H-1,2-oxazine-N-oxides with Arynes Научная публикация

Журнал

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Вых. Данные

Год: 2022, Том: 87, Номер: 10, Страницы: 6838-6851 Страниц : 14 DOI: 10.1021/acs.joc.2c00515

Авторы

Lukoyanov Alexander A. ¹ , Tabolin Andrey A. ¹ , Nelyubina Yulia V. ² , Ioffe Sema L. ¹ , Sukhorukov Alexey Yu. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect, 47, Moscow 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilov strasse 28, Moscow 119991, Russian Federation

Six-membered cyclic nitronates (5,6-dihydro-4H-1,2-oxazine-N-oxides) react with Kobayashi’s aryne precursors producing 3-(2-hydroxyaryl)-substituted 1,2-oxazines via deoxygenative C–H arylation. The process involves a hitherto unknown 1,3-dipolar cycloaddition of nitronate to the aryne to give an unusual tricyclic nitroso acetal, in which the N–O bond of the isoxazoline ring is selectively cleaved upon the action of a base (CsF) or an acid (TFA). The transient cycloadducts were isolated and characterized in some cases. The synthetic potential of the obtained 3-(2-hydroxyaryl)-substituted 1,2-oxazines was demonstrated by their stereoselective reduction to 1,4-amino alcohols and reductive 1,2-oxazine ring contraction to tetrahydrofuran derivatives.

Lukoyanov A.A. , Tabolin A.A. , Nelyubina Y.V. , Ioffe S.L. , Sukhorukov A.Y.
Deoxygenative Arylation of 5,6-Dihydro-4H-1,2-oxazine-N-oxides with Arynes
Journal of Organic Chemistry. 2022. V.87. N10. P.6838-6851. DOI: 10.1021/acs.joc.2c00515 WOS Scopus OpenAlex

Web of science:	WOS:000805365600026
Scopus:	2-s2.0-85130316196
OpenAlex:	W4229016191

БД	Цитирований
OpenAlex	7
Scopus	7
Web of science	6