A comparison of ring-chain tautomerism in heterocycles derived from 2-aminobenzenesulfonamide and anthranilamide

A number of anthranilamide and 2-aminobenzenesulfonamide derivatives with aromatic aldehydes and 1,3-dicarbonyl compounds were synthesized. Substituted benzaldehyde derivatives of neither aminoamides showed tautomerism in solutions. Reaction products of 2-aminobenzenesulfonamide with p-substituted b...

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Bibliographic Details
Published in:Tetrahedron 2005-07, Vol.61 (30), p.7294-7303
Main Authors: Maloshitskaya, Olga A., Sinkkonen, Jari, Alekseyev, Valery V., Zelenin, Kirill N., Pihlaja, Kalevi
Format: Article
Language:English
Subjects:
1,3-Dicarbonyl compounds
2-Aminobenzenesulfonamide
Anthranylamide
Ring-chain tautomerism
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Summary:A number of anthranilamide and 2-aminobenzenesulfonamide derivatives with aromatic aldehydes and 1,3-dicarbonyl compounds were synthesized. Substituted benzaldehyde derivatives of neither aminoamides showed tautomerism in solutions. Reaction products of 2-aminobenzenesulfonamide with p-substituted benzoylacetic aldehydes and p-substituted benzoylacetones undergo ring-chain tautomerism with a good linear correlation between the ring-chain equilibrium constants (log K, where K=[ring]/[chain]) and the Hammett–Brown σ + parameters of the aromatic substituents. The equilibrium constant was measured for the reaction products of 2-aminobenzenesulfonamide with unsubstituted benzoylacetaldehyde at several temperatures which enabled the enthalpy and entropy of this reaction to be evaluated. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.04.074