Versatile synthesis of oxindole-1,3-dicarboxamides |
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Authors: | Márta Porcs-Makkay Balázs Volk Gyula Simig |
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Institution: | a EGIS Pharmaceuticals Plc., Chemical Research Division, PO Box 100, H-1475 Budapest, Hungary b University of Szeged, Faculty of Education, Boldogasszony Str. 6, H-6725 Szeged, Hungary |
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Abstract: | A new, high-yielding synthesis of oxindole-1,3-dicarboxamides was elaborated starting from 1-phenoxycarbonyl-3-ethoxycarbonyl-2-oxindole and 1,3-diphenoxycarbonyl-2-oxindole. This method permits also the preparation of N,N,N′-tri- and N,N,N′,N′-tetrasubstituted oxidole-1,3-dicarboxamides, families of compounds that are unknown in the literature. The scope and limitations of the methodology have also been investigated, and a remarkable selectivity has been observed among the amines used in the amidation steps. |
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Keywords: | Oxindole Amidation Regioselectivity Keto/enol equilibrium Aminolysis |
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