The IMDAV reaction between 3-(isoxazol-3-yl)allylamines and maleic anhydrides: an unusual approach to pyrrolo[3,4-<i>c</i>]pyridine derivatives, possessing anti-inflammatory activity

An unexpected cascade of <i>N</i>-acylation/intramolecular [4 + 2] cycloaddition/decarboxylation/isoxazole ring-opening reactions is observed in the course of the interaction between 3-(isoxazol-3-yl)allylamines and maleic or trifluoromethylmaleic anhydrides. This four-step sequence begins with the initial <i>N</i>-acylation of allylamines by the anhydride, followed by an intramolecular Diels-Alder reaction, which is accompanied by spontaneous decarboxylation, and ends with the opening of the isoxazole ring. As a result, an original approach to a pyrrolo[3,4-<i>c</i>]pyridine core was discovered. A test series of pyrrolo[3,4-<i>c</i>]pyridin-3-ones was investigated for anti-inflammatory activity and cytotoxicity, including the ability to inhibit NLRP3 inflammasome activation.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00040h
Citations
4
Primary Topic
Synthesis and Reactions of Organic Compounds
Type
article
Field-Weighted Citation Impact
3.74
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article

The IMDAV reaction between 3-(isoxazol-3-yl)allylamines and maleic anhydrides: an unusual approach to pyrrolo[3,4-c]pyridine derivatives, possessing anti-inflammatory activity

Valentina V. Ilyushenkova, Федор И. Зубков, В. И. Поткин, Roman Litvinov et al.
4 citations
Organic & Biomolecular Chemistry
Synthesis and Reactions of Organic Compounds
3.74
article

The IMDAV reaction between 3-(isoxazol-3-yl)allylamines and maleic anhydrides: an unusual approach to pyrrolo[3,4-c]pyridine derivatives, possessing anti-inflammatory activity

Valentina V. Ilyushenkova, Федор И. Зубков, В. И. Поткин, Roman Litvinov, Vladimir P. Zaytsev, Роман А. Новиков, Mikhail S. Grigoriev, Daria N. Simakova, Ирина А. Колесник, Roman D Danilov, Viktoria S Maslova
article en
4 citations

Abstract

An unexpected cascade of <i>N</i>-acylation/intramolecular [4 + 2] cycloaddition/decarboxylation/isoxazole ring-opening reactions is observed in the course of the interaction between 3-(isoxazol-3-yl)allylamines and maleic or trifluoromethylmaleic anhydrides. This four-step sequence begins with the initial <i>N</i>-acylation of allylamines by the anhydride, followed by an intramolecular Diels-Alder reaction, which is accompanied by spontaneous decarboxylation, and ends with the opening of the isoxazole ring. As a result, an original approach to a pyrrolo[3,4-<i>c</i>]pyridine core was discovered. A test series of pyrrolo[3,4-<i>c</i>]pyridin-3-ones was investigated for anti-inflammatory activity and cytotoxicity, including the ability to inhibit NLRP3 inflammasome activation.

Organic & Biomolecular ChemistryVol. 23(16)
Engelhardt Institute of Molecular Biology (RU), Peoples' Friendship University of Russia (RU), National Academy of Sciences of Belarus (BY), Volgograd State Medical University (RU), Innovate UK (GB), Russian New University (RU), Frumkin Institute of Physical Chemistry and Electrochemistry Russian Academy of Sciences (RU), N.D. Zelinsky Institute of Organic Chemistry (RU), Volgograd Institute of Business (RU)
Openalex Percentile: Top 8%
Synthesis and Reactions of Organic Compounds
3.74
DOISourceOpenAlex
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