Unexpected ring‑opening of 2,3‑dihydropyridines

Hoffelner, M. H. and Seebacher, W. and Kaiser, M. and Mäser, P. and Pferschy-Wenzig, E. M. and Saf, R. and Belaj, F. and Kretschmer, N. and Alajlani, M. and Brantner, A. and Bauer, R. and Weis, R.. (2021) Unexpected ring‑opening of 2,3‑dihydropyridines. Monatshefte für Chemie, 152. pp. 1347-1359.

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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.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel and Mäser, Pascal
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:06 Jun 2023 15:59
Deposited On:20 Dec 2022 10:42

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