Hydrolysis of ureas. Kinetics and mechanism of the basic hydrolysis of indole‐1‐carboxamides and (5 H ‐dibenz[ b,f ]azepine)‐5‐carboxamide | Zendy

Linda Paolo | Zendy; Ebert Cynthia | Zendy; Lovrecich Mara | Zendy; Rubessa Fulvio | Zendy

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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.

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