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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 9
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SYNTHETIC COMMUNICATIONS REVIEWS

The 1,3-dipolar cycloaddition of adamantine-derived nitrones with maleimides

Alexander P. MolchanovInstitute of Chemistry Saint Petersburg State University, St. Petersburg, Russian Federation; Correspondence[email protected]
,
Valentina M. LukinaInstitute of Chemistry Saint Petersburg State University, St. Petersburg, Russian Federation;
,
Mariia M. EfremovaInstitute of Chemistry Saint Petersburg State University, St. Petersburg, Russian Federation;
,
Anna A. MurylevaSaint Petersburg Pasteur Institute, St. Petersburg, Russian Federation
,
Alexander V. SlitaSaint Petersburg Pasteur Institute, St. Petersburg, Russian Federation
&
Vladimir V. ZarubaevSaint Petersburg Pasteur Institute, St. Petersburg, Russian Federation
Pages 1367-1374 | Received 17 Jan 2020, Published online: 19 Mar 2020
 
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Abstract

Adamantane-derived aldo- and ketonitrones react with maleimides giving corresponding isoxazolidines. In the case of aldonitrones reactions proceed giving the diastereomeric mixtures. The ratio of isomers is changing during the reaction process due to the reversibility of the cycloaddition reaction. The cytotoxic and virus-inhibiting activity against influenza virus was investigated for selected adducts.

Graphical Abstract

Acknowledgments

NMR, HRMS and IR studies were performed at the Saint Petersburg State University Center for Magnetic Resonance, Center for Chemical Analysis and Materials Research and Chemistry Educational Centre, respectively.

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