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

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

Journal

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

Output data

Year: 2022, Volume: 87, Number: 10, Pages: 6838-6851 Pages count : 14 DOI: 10.1021/acs.joc.2c00515

Authors

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

Affiliations

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

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OpenAlex	7
Scopus	7
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