Unexpected ring-opening of 2,3-dihydropyridines

The reaction of 2,3-dihydropyridines with sulfonyl halides surprisingly yielded open chain dienes with sulfonylimine structure. The products were specific out of several possible isomers and, therefore, a separation of isomers was not necessary. All new compounds were characterized using FT-IR spect...

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Veröffentlicht in:Monatshefte für Chemie 2021-11, Vol.152 (11), p.1377-1387
Hauptverfasser: Hoffelner, Michael-Hannes, Seebacher, Werner, Kaiser, Marcel, Mäser, Pascal, Pferschy-Wenzig, Eva-Maria, Saf, Robert, Belaj, Ferdinand, Kretschmer, Nadine, Alajlani, Muaaz, Brantner, Adelheid, Bauer, Rudolf, Weis, Robert
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Sprache:eng
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Zusammenfassung:The reaction of 2,3-dihydropyridines with sulfonyl halides surprisingly yielded open chain dienes with sulfonylimine structure. The products were specific out of several possible isomers and, therefore, a separation of isomers was not necessary. All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. A bicyclic by-product from the reaction of a 2,3-dihydropyridine with mesyl chloride was isolated and its structure elucidated using a single X-ray crystal analysis. Some biological activities, like antimicrobial and cytotoxic properties were investigated. Graphic abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-021-02850-3