Scope and limitations of the synthesis of functionalized quinolizidinones and related compounds by a simple precursor approach via addition of lithium allylmagnesates to 2-pyridones and RCM as key steps |
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Authors: | Jacek G Sośnicki Łukasz Struk Tomasz Idzik Gabriela Maciejewska |
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Institution: | 1. West Pomeranian University of Technology, Szczecin, Institute of Chemistry and Environmental Protection, Al. Piastów 42, 71-065 Szczecin, Poland;2. Wroc?aw University of Technology, Faculty of Chemistry, Wybrze?e Wyspiańskiego 27, 50-370 Wroc?aw, Poland |
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Abstract: | The scope and limitations of the simple synthesis of functionalized quinolizidin-4-ones by chemoselective N-alkenylation of NH pyridin-2(1H)-ones (2-pyridones), regioselective addition of lithium allyl(di-n-butyl)magnesates(1-) to N-alkenylpyridin-2(1H)-ones, followed by ring closing metathesis (RCM) is described. A number of functionalizations introduced into quinolizidin-4-one rings demonstrated the high prospect of the strategy proposed in scaffold synthesis. Their extension to the syntheses of pyrido1,2-a]azepin-4-one and pyrido1,2-a]azocin-4-one derivatives as well as to spiro-fused compounds is also presented. |
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Keywords: | Quinolizidinones Magnesates Regioselectivity Nucleophilic addition Metathesis |
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