| 第 35 卷第 6 期 |  | Vol. 35 No. 6 | | 2005 年 12 月 | Dec 2005 |
|
所属栏目：医药及中间体
(2,6-二氯-5-氟-吡啶-3-羰基)-乙酸乙酯的合成 |
| 陈磊; 高忠良; 刘雁; 朱秋峰(河北工业大学应用化学系) |
| 摘 要：(2,6-二氯-5-氟-吡啶-3-羰基)-乙酸乙酯是合成沙星类药物和其他喹诺酮类抗菌药的关键中间体。以2,6-二氯-5-氟-吡啶-3-羧酸,二氯亚砜为原料发生亲核取代反应制得2,6-二氯-5-氟-吡啶-3-酰氯;以β二羰基化合物丙二酸二乙酯与乙醇镁反应生成强亲核试剂[C2H(COOC2H5)2]-碳负离子;它再与2,6-二氯-5-氟-吡啶-3-酰氯发生亲核取代反应制得(2,6-二氯-5-氟-吡啶-3-羰基)丙二酸乙酸乙酯;在对甲苯磺酸的作用下经过酯的水解和β-二酸的脱羧得目的产物(2,6-二氯-5-氟-吡啶-3-羰基)-乙酸乙酯。对反应条件进行了改进,选用了比较廉价的原料,并对重结晶试剂进行了深入的筛选,得到具有良好晶形的目的产物。 |
| 关键词：喹诺酮; （2; 6-二氯-5-氟-吡啶-3-羰基）-乙酸乙酯; 结晶; 碳负离子 |
| 中图分类号：TQ253.21 文献标识码：A 文章编号：1009-9212(2005)06-0029-03 |
|
| Synthesis of ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxo-propionate |
| CHEN Lei; GAO Zhong-liang; LIU Yan; ZHU Qiu-feng（School of Chemical Engineering; Hebei University of Technology; Tianjin 300130; China） |
| Abstract：Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxo-propionate is the key of the synthesis of Quinolone antibacterial agents.2,6-dichloro-5-fluoro-nicotine acid was treated with Sulphurous oxychloride,to give 2,6-dichloro-5-fluoronicotinoyl chloride,then reacted to carbanion.The resultant was treated with p-Toluenesulfonic acid,to give the resultant we need.We improve on the reaction,using the cheap material,and selected the best one of the reagent to give the best of the resultant with nicer crystal. |
| Key words：quinolone; ethyl 3-（2; 6-dichloro-5-fluoropyridin-3-yl）-3-oxo-propionate; crystal carbanion |
|
收稿日期：2005-08-27
|
| 阅读全文 |
|