A comparison of ring-chain tautomerism in heterocycles derived from 2-aminobenzenesulfonamide and anthranilamide
A comparison of ring-chain tautomerism in heterocycles derived from 2-aminobenzenesulfonamide and anthranilamide
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DOI：
10.1016/j.tet.2005.04.074
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发表时间：
2005-07-25
期刊：
影响因子：
2.1
通讯作者：
Pihlaja, K
中科院分区：
文献类型：
--
作者：
Maloshitskaya, OA;Sinkkonen, J;Pihlaja, K
合成了多种邻氨基苯甲酰胺和2-氨基苯磺酰胺与芳香醛和1,3-二羰基化合物的衍生物。两种氨基酰胺的取代苯甲醛衍生物在溶液中均不表现出互变异构现象。 2-氨基苯磺酰胺与对位取代苯甲酰乙醛和对位取代苯甲酰丙酮的反应产物发生环链互变异构，环链平衡常数（log K，其中K = [环]/[链]）与芳香族取代基的Hammett-Brown sigma(+)参数之间具有良好的线性相关性。在几个温度下测量 2-氨基苯磺酰胺与未取代的苯甲酰乙醛的反应产物的平衡常数，从而能够评估该反应的焓和熵。 (c) 2005 Elsevier Ltd. 保留所有权利。
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 sigma(+) 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. (c) 2005 Elsevier Ltd. All rights reserved.