绿色合成抗癫痫药氯西加酮及其类似物有机化学.pdfVIP

DOI: 10.6023/cjoc201305005 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 绿色合成抗癫痫药氯西加酮及其类似物 刘改枝*,a 吴 亚a 徐海伟b 刘宏民*,b (a 河南中医学院药学院 郑州 450046) (b 郑州大学药学院 郑州 450001) 摘要 用温和高效的方法实现了抗癫痫药氯西加酮及其系列类似物的非对映选择性绿色合成. 4- 甲氧基呋喃酮与芳香 醛发生类似 Aldol 缩合的反应合成系列氯西加酮类似物. 通过结晶的方法高选择性地得到(de ≥96%)氯西加酮. 在反应 1 13 体系中引入手性诱导试剂实现氯西加酮的非对映选择性合成. 所有新化合物的结构都经过 H NMR, C NMR, IR, HRMS 确认. 关键词 绿色合成; 氯西加酮; 合成; 抗癫痫药; 非对映选择性 A Green Route for the Synthesis of Antiepileptic Drug Losigamone and Its Analogues Liu, Gaizhi*,a Wu, Yaa Xu, Haiweib Liu, Hongmin*,b a ( Henan University of Traditional Chinese Medicine, Zhengzhou 450046) b ( School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001) Abstract By an efficient and mild diastereoselective aldol-type reaction of aromatic aldehyde with 4-methoxyfuran- 2(5H)-one, losigamone and a series of its analogues were synthesized. Fortunately, the racemic threo-isomers of losigamone were obtained by crystallization with good de value ( ≥96%). The introduction of chiral reagents to the reaction system re- sulted in diastereoselectivity to losigamone. All structures of new compounds were confirmed by 1H NMR, 13C NMR, IR and HRMS techniques. Keywords