L-脯氨酸催化合成1,4-二氢吡啶和1,8-二氧代十氢吖啶

L-Proline Catalyzed Synthesis of 1,4-Dihydropyridine and 1,8-Dioxodecahydroacridine Derivatives

含1,4-二氢吡啶和1,8-二氧代十氢吖啶分子片段的化合物具有扩张血管、抗菌和抗肿瘤等活性。因此,探讨该类衍生物绿色合成方法成为药物合成领域的热点之一。基于有机小分子催化剂L-脯氨酸廉价易得、无毒无害和水溶性等特点,结合微波辐射技术快速高效等优势,以芳香醛、β-二酮(乙酰乙酸乙酯/二甲基环己二酮)和乙酸铵为原料,乙醇为溶剂,催化剂用量20 mol/mol,微波功率300 W和80℃的条件下,通过成环缩合反应“一锅法”合成了目标化合物,收率达80%~93%。该方法具有条件温和、操作简单以及环境友好等优点。

Functionalized 1,4-dihydropyridine and 1,8-dioxodecahydroacridine exhibit a wide range of pharmacological properties such as vasodilators,antimicrobial and antitumour activities.Therefore,the development of a green,easy efficient method for the preparation demands serious attention.In view of L-proline as a remarkable organocatalyst with cheap,eco-friendly and water-soluble characteristics,along with the fast and significant efficiency of microwave-promoted in green chemistry,some 1,4-dihydropyridine and 1,8-dioxodecahydroacridine derivatives were synthesized from the aromatic aldehydes with ethyl acetoacetate(or 5,5-dimethylcyclohexane-1,3-dione)and ammonium acetate by the one-pot method under microwave irradiation was described.The results indicated that the catalyst is efficient with the amount of 20 mol/mol in solvent of ethanol under irradiation at 300 W with a temperature of 80℃to afford the target products with good yields of 80%~93%,respectively.The advantages of this procedure are its mild reaction condition,easy work-up and environmentally benign nature.