1. Unexpected ring-opening of 2,3-dihydropyridines
- Author
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Marcel Kaiser, Nadine Kretschmer, Werner Seebacher, Muaaz Alajlani, Adelheid Brantner, Robert Saf, Pascal Mäser, Robert Weis, Rudolf Bauer, Ferdinand Belaj, Michael-Hannes Hoffelner, and Eva-Maria Pferschy-Wenzig
- Subjects
Sulfonyl ,chemistry.chemical_classification ,Bicyclic molecule ,Chemistry ,Halide ,General Chemistry ,Nuclear magnetic resonance spectroscopy ,Ring (chemistry) ,Chloride ,Combinatorial chemistry ,Crystal ,medicine ,Spectroscopy ,medicine.drug - Abstract
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
- Published
- 2021