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Hydrolysis of ureas. Kinetics and mechanism of the basic hydrolysis of indole‐1‐carboxamides and (5 H ‐dibenz[ b,f ]azepine)‐5‐carboxamide
Author(s) -
Linda Paolo,
Ebert Cynthia,
Lovrecich Mara,
Rubessa Fulvio
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210157
Subject(s) - chemistry , azepine , carboxamide , indole test , hydrolysis , medicinal chemistry , kinetics , hydroxide , reaction rate constant , stereochemistry , organic chemistry , physics , quantum mechanics
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‐‐2.4 N . 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, (5 H ‐dibenz[ b,f ]azepine)‐5‐carboxamide, a potent anticonvulsant drug, is particularly stable under these conditions.