Nucleophilic properties of a nonstabilized azomethine ylide derived from sarcosine and cyclohexanone. A novel domino reaction leading to substituted 4-aryl-2-pyrrolidones |
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Authors: | Vladimir S. Moshkin,Vyacheslav Ya. SosnovskikhGerd-Volker Rö schenthaler |
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Affiliation: | a Department of Chemistry, Ural Federal University, pr. Lenina 51, 620083 Ekaterinburg, Russia b School of Engineering and Science, Jacobs University Bremen, 28759 Bremen, Germany |
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Abstract: | A nonstabilized asymmetric azomethine ylide derived from sarcosine and cyclohexanone reacts with 3-substituted coumarins and ethyl benzylidene malonate to give 4-aryl-2-pyrrolidones in moderate yields, and the adducts of classical 1,3-dipolar cycloadditions as the minor products. The main reaction proceeds via a domino process, starting with 1,4-nucleophilic addition to the conjugated double bond, and represents the first example of the nucleophilic properties of a nonstabilized azomethine ylide. |
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Keywords: | Nonstabilized asymmetric azomethine ylide Domino reaction 4-Aryl-2-pyrrolidones 1,4-Nucleophilic addition 3-Substituted coumarins [3+2] Cycloaddition |
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