查尔酮异甘草素Mannich碱类化合物的合成

Synthesis Mannich basic chalcone compounds

目的采用Mannich反应合成查尔酮异甘草素Mannich碱类化合物。方法以间苯二酚、甲醛为原料,以两种含氮的化合物(叔丁胺和吡咯烷)为胺类物质,探索间苯二酚Mannich反应的最佳条件;并利用异甘草素中的间苯二酚结构进行Mannich反应,以醋酸为溶媒,浓盐酸作催化剂的条件下合成含氮的Mannich碱的目标化合物查尔酮。结果在间苯二酚Mannich反应的基础上合成4个异甘草素类化合物,其结构经NMR谱确认为3-乙醇胺-异甘草素、3-吡咯烷-异甘草素、3-叔丁胺-异甘草素、3-吗菲林-异甘草素。制备目标化合物,酚∶醛∶胺比例按1∶2∶4时产率最高。结论本研究为甘草查尔酮类化合物的合成研究奠定了基础。

Objective A series of chalcone compounds were synthesized by Mannich reaction. Methods The best condition of the resorcinol Mannich reaction were explored with resorcinol and formaldehyde as mate- rials, with two kinds of nitrogenous compounds （tert-butylamine and pyrrolidine） as the amines; then the target compounds （2＇, 4＇-dihydroxy-4-fluoro-3＇- pyrrolidine methyl chalcone ketones） were synthesised with acetic acid as solvent, concentrated hydrochloric acid as catalyst. Results The 4 isoliquiritigenin com- pounds on the basis of the resorcinol Mannich reaction were 3-ethanolamine-isoliquiritigenin, 3- pyrrolidone-isoliquiritigenin, 3-tert-butylamine-isoliquiritigenin, 3-morpholine-isoliquiritigenin, whose structures were confirmed by NMR spectroscopy. When phenol ＂ aldehyde ： amine was 1：2 ： 4, the rate of production was the highest in the preparation of target compounds. Conclusion This study laid a foun-dation for the synthesis of chalcone compounds.