Novel Acid-Catalyzed Transformation of 1-Benzyl-3-Chloro-5-Hydroxy-4-[(4-Methylphenyl)Sulfanyl]-1,5-Dihydro-2<i>H</i>-Pyrrol-2-One
Nitrogen-containing heterocycles of 3-pyrrolin-2-one series are widely represented in natural and synthetic compounds, with a broad spectrum of pharmacological activity and considerable potential in medicinal and synthetic organic chemistry. In this communication, we report the previously unknown ac...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-06-01
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| Series: | Molbank |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-8599/2025/2/M2017 |
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| Summary: | Nitrogen-containing heterocycles of 3-pyrrolin-2-one series are widely represented in natural and synthetic compounds, with a broad spectrum of pharmacological activity and considerable potential in medicinal and synthetic organic chemistry. In this communication, we report the previously unknown acid-catalyzed transformation of a <i>N</i>-substituted derivative of 3-pyrrolin-2-one that generates two types of heterocyclic moieties. The reflux of 1-benzyl-3-chloro-5-hydroxy-4-[(4-methylphenyl)sulfanyl]-1,5-dihydro-2<i>H</i>-pyrrol-2-one in toluene in the presence of catalytic amounts of H<sub>2</sub>SO<sub>4</sub> resulted in the formation of a mixture of 1-benzyl-3-[(4-methylphenyl)sulfanyl]-1<i>H</i>-pyrrole-2,5-dione and 1-benzyl-7-methyl-1<i>H</i>-benzo[4,5]thieno[3,2-<i>b</i>]pyrrole-2,3-dione. The structures of four novel nitrogen-containing heterocycles were elucidated through IR, NMR spectroscopy and HRMS spectrometry. A new derivative of the fused tricyclic compounds, possessing benzo[<i>b</i>]thiophene and pyrrole-1,2-dione fragments, was also characterized by single-crystal X-ray diffraction. |
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| ISSN: | 1422-8599 |