Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

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 d...

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Autores principales: Karcev, Dmitriy D., Efremova, Mariia M., Molchanov, Alexander P., Rostovskii, Nikolai V., Kryukova, Mariya A., Bunev, Alexander S., Khochenkov, Dmitry A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9603865/
https://www.ncbi.nlm.nih.gov/pubmed/36293495
http://dx.doi.org/10.3390/ijms232012639
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author Karcev, Dmitriy D.
Efremova, Mariia M.
Molchanov, Alexander P.
Rostovskii, Nikolai V.
Kryukova, Mariya A.
Bunev, Alexander S.
Khochenkov, Dmitry A.
author_facet Karcev, Dmitriy D.
Efremova, Mariia M.
Molchanov, Alexander P.
Rostovskii, Nikolai V.
Kryukova, Mariya A.
Bunev, Alexander S.
Khochenkov, Dmitry A.
author_sort Karcev, Dmitriy D.
collection PubMed
description 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.
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spelling pubmed-96038652022-10-27 Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines Karcev, Dmitriy D. Efremova, Mariia M. Molchanov, Alexander P. Rostovskii, Nikolai V. Kryukova, Mariya A. Bunev, Alexander S. Khochenkov, Dmitry A. Int J Mol Sci Article 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. MDPI 2022-10-20 /pmc/articles/PMC9603865/ /pubmed/36293495 http://dx.doi.org/10.3390/ijms232012639 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Karcev, Dmitriy D.
Efremova, Mariia M.
Molchanov, Alexander P.
Rostovskii, Nikolai V.
Kryukova, Mariya A.
Bunev, Alexander S.
Khochenkov, Dmitry A.
Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines
title Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines
title_full Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines
title_fullStr Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines
title_full_unstemmed Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines
title_short Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines
title_sort selective and reversible 1,3-dipolar cycloaddition of 2-(2-oxoindoline-3-ylidene)acetates with nitrones in the synthesis of functionalized spiroisoxazolidines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9603865/
https://www.ncbi.nlm.nih.gov/pubmed/36293495
http://dx.doi.org/10.3390/ijms232012639
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