Hydrolysis of ureas. Kinetics and mechanism of the basic hydrolysis of indole-1-carboxamides and (5H-dibenz[b,f]azepine)-5-carboxamide |
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| Authors: | Paolo Linda Cynthia Ebert Mara Lovrecich Fulvio Rubessa |
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| Institution: | 1. Istituto di Chimica, Università di Trieste Italy;2. Istituto di Chimica Farmaceutica, Università di Trieste, Italy |
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| Abstract: | The hydroxide ion catalyzed hydrolysis of indole-1-carboxamide and indole-1-(N,N-dimethyl)carboxamide has been studied in water at 60.0° and OH?] concentration between 0.3--2.4N. The rate constants of formation of the tetrahedral intermediate are strongly increased by N-substitution with a heteroaromatic ring in comparison with simple amides. Carbamazepine, (5H-dibenzb,f]azepine)-5-carboxamide, a potent anticonvulsant drug, is particularly stable under these conditions. |
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