Convenient synthesis of 3-unsubstituted oxindole-1-carboxamides |
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Authors: | Márta Porcs-Makkay Balázs Volk Eszter Kókai Gyula Simig |
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Affiliation: | 1. EGIS Pharmaceuticals Plc., Chemical Research Division, PO Box 100, H-1475 Budapest, Hungary;2. Budapest University of Technology and Economics, Faculty of Chemical Engineering, PO Box 91, 1521 Budapest, Hungary |
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Abstract: | The multiple reactivity of the mesomeric anion formed by N- or C(3)-deprotonation of 3-unsubstituted oxindoles hampers the selective introduction of substituents onto the nitrogen atom. A conveniently applicable reaction sequence has been elaborated for the synthesis of 3-unsubstituted oxindole-1-carboxamides starting from the easily available 1,3-bis(phenoxycarbonyl)oxindoles. Selective amidation of the N-phenoxycarbonyl moiety and subsequent removal of the C(3)-phenoxycarbonyl moiety furnished the title compounds, which are useful building blocks for further functionalization. Besides the novel methodologies, several new representatives of this valuable compound family and their intermediates are also described below. |
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