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Nucleophilic behavior of DBU in a conjugate addition reaction
Affiliation:1. Department of Chemical Engineering, Yibin University, Yibin, 644000, People’s Republic of China;2. BioBioPha Co., Ltd., Kunming, 650201, People’s Republic of China;3. Department of Chemical Science & Technology, Kunming University, Kunming 650214, People’s Republic of China;1. Institut für Pharmazeutische und Medizinische Chemie der Westfälischen Wilhelms-Universität Münster, Corrensstraße 48, D-48149 Münster, Germany;2. Research Center for Materials Science and Department of Chemistry, Nagoya University, Chikusa-ku, Nagoya 464-8602, Japan;3. Cells-in-Motion Cluster of Excellence (EXC 1003—CiM), University Münster, Germany;1. Department of Medicinal Chemistry, Jagiellonian University Medical College, Kraków, Poland;2. Department of Pharmacodynamics, Chair of Pharmacodynamics, Jagiellonian University Medical College, Kraków, Poland;3. Department of Radioligands, Jagiellonian University Medical College, Kraków, Poland
Abstract:Reaction of DBU with a diarylpyrone results in 1,4 addition of the DBU and subsequent fragmentation of the DBU moiety into an aminopropyl caprolactam. Incorporation of the fragmented DBU into the diarylpyridone is postulated to occur by an addition/elimination pathway.
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