新型吖啶酮酰胺衍生物的合成

Synthesis of Novel Acridone Carboxamide Derivatives

以2-氨基-5-甲基苯甲酸为原料,与4-碘苯甲酸发生Ullmann偶联反应得到2-二取代胺基苯甲酸,在浓硫酸作用下发生分子内傅克酰基化得到吖啶酮二甲酸粗品,后在乙醇中酯化,柱层析得到吖啶酮二甲酸乙酯。将其在碱性条件下水解并酸化后,与不同的胺类反应得到新型吖啶酮酰胺衍生物。目标化合物的结构经^(1)H NMR、^(13)C NMR和HRMS确证。

2-disubstituted aminobenzoic acids were obtained by using 2-amino-5-methyl benzoic acids as starting materials to react with 4-iodobenzoic acid by the Ullmann coupling reaction,which were then treated in concentrated sulfuric acid to afford the crude acridone dicarboxylic acids by the intramolecular Friedel-Crafts acylation reaction.The crude acridone acids were reacted with ethanol and then purified to give the ethyl acridone dicarboxylate.The obtained esters were hydrolyzed in alkaline environment and then acidified to proceed the target acridone acid,which could react with various amines to afford five novel acridone amide derivative.The structures of target compounds were characterized by ^(1)H NMR,^(13)C NMR and HRMS.