3-Halo-5,6-dihydro-4H-1,2-oxazine N-oxides as synthetic equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles

3-Halo-5,6-dihydro-4H-1,2-oxazine N-oxides as synthetic equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2024, Volume: 22, Number: 18, Pages: 3615-3621 Pages count : 7 DOI: 10.1039/d4ob00391h

Authors

Lukoyanov Alexander A. ¹ , Aksenova Svetlana A. ² , Tabolin Andrey A. ¹ , Sukhorukov Alexey Yu. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow, 119334, Russian Federation

The reaction of 3-halo-5,6-dihydro-4H-1,2-oxazine N-oxides with arynes was studied. Arynes were generated from o-silylaryl triflates and underwent consecutive [3 + 2]-cycloaddition/[4 + 2]-cycloreversion with N-oxides leading to substituted 3-vinyl-benzisoxazoles in high yields. In the presented sequence, 1,2-oxazine N-oxides act as surrogates of rarely employed unsaturated nitrile oxides. A broad substrate scope was demonstrated. The influence of the substitution pattern of an aryne on the reaction outcome was determined. In the presence of bulky substituents, polycyclic 4,4a-dihydro-3H-benzofuro[3,2-c][1,2]oxazines were selectively formed. Mechanistic schemes for the observed reaction pathways were proposed. The synthetic utility of the products was demonstrated by their follow-up modifications.

Lukoyanov A.A. , Aksenova S.A. , Tabolin A.A. , Sukhorukov A.Y.
3-Halo-5,6-dihydro-4H-1,2-oxazine N-oxides as synthetic equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles
Organic & Biomolecular Chemistry. 2024. V.22. N18. P.3615-3621. DOI: 10.1039/d4ob00391h WOS Scopus OpenAlex

Web of science:	WOS:001205074500001
Scopus:	2-s2.0-85190722919
OpenAlex:	W4394679174

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