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- Title
Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines.
- Authors
Karcev, Dmitriy D.; Efremova, Mariia M.; Molchanov, Alexander P.; Rostovskii, Nikolai V.; Kryukova, Mariya A.; Bunev, Alexander S.; Khochenkov, Dmitry A.
- Abstract
The 1,3-dipolar cycloaddition of 2-(2-oxoindoline-3-ylidene)acetates with functionalized aldo- and ketonitrones proceeds with good selectivity to provide new highly functionalized 5-spiroisoxazolidines. A characteristic feature of these reactions is reversibility that allows for the control of the diastereoselectivity of cycloaddition. The reduction of obtained adducts using zinc powder in acetic acid leads to 1,3-aminoalcohols or spirolactones. For a number of the spiro compounds obtained, anticancer activity was found.
- Subjects
ISOXAZOLIDINES; NITRONES; RING formation (Chemistry); ZINC powder; ACETATES; SPIRO compounds; ACETIC acid
- Publication
International Journal of Molecular Sciences, 2022, Vol 23, Issue 20, p12639
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms232012639