Abstract

In this work, we report the synthesis of new pyrazole derivatives bearing amide and sulfonamide frameworks from aza-aurones. Firstly, the intermediate spiropyrazolines were obtained through a highly regioselective 1,3-dipolar cycloaddition of nitrilimines with aza-aurones. Subsequently, the obtained cycloadducts were subjected to hydrochloric acid in hot ethanol which conducts to 5-(2-aminobenzoyl)-3,4-diaryl-1-phenylpyrazoles. Finally, the target compounds were obtained separately by the action of acetic anhydride, benzoyl chloride and tosyl chloride on the intermediates 2-aminobenzoylpyrazoles, respectively. Structures of all the synthesized compounds were established using IR, ¹H NMR and ¹³C NMR and mass spectroscopy.

Graphic Abstract

Synthesis and characterization of novel heterocyclic systems encompassing pyrazole derivatives from aza-aurones are reported. The synthetic routes used in this work are efficient and relevant, involving the 1,3-dipolar cycloaddition and alkylation reactions. The outcomes show that spectroscopic data fit the structure of all synthesized compounds.

中文翻译：

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设计，合成和表征含氮杂-金龙酰胺和磺酰胺部分的官能化吡唑衍生物

摘要

在这项工作中，我们报告了从氮杂-金龙酸酯合成带有酰胺和磺酰胺骨架的新型吡唑衍生物。首先，中间体螺并吡唑啉是通过亚硝基胺与氮杂-金酮的高度区域选择性的1，3-偶极环加成反应获得的。随后，将获得的环加合物在热乙醇中经受盐酸处理，该热乙醇可传导生成5-（2-氨基苯甲酰基）-3,4-二芳基-1-苯基吡唑。最后，分别通过乙酸酐，苯甲酰氯和甲苯磺酰氯对中间体2-氨基苯甲酰基吡唑的作用分别获得目标化合物。使用IR，¹ H NMR和¹³ C NMR以及质谱确定所有合成化合物的结构。

图形摘要

据报道，新型合成杂环系统涵盖了来自氮杂-金酮的吡唑衍生物。在这项工作中使用的合成路线是有效和相关的，涉及1,3-偶极环加成和烷基化反应。结果表明，光谱数据符合所有合成化合物的结构。