文献类型：期刊文献

中文题名：氯化两面针碱合成方法的改进

英文题名：Process Improvement on the Synthesis of Nitidine Chloride

作者：许旭升[1,2];刘志千[2];邵文浩[2];叶霁[2];孙青龑[2];何薇薇[1];张卫东[1,2]

机构：[1]华东理工大学药学院,上海200237;[2]第二军医大学药学院,上海200433

年份：2015

卷号：35

期号：6

起止页码：1353

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;WOS:【SCI-EXPANDED(收录号:WOS:000359274400019)】；北大核心:【北大核心2014】；CSCD:【CSCD2015_2016】；

基金：Project supported by the NSFC (No. 81230090), the Shanghai Leading Academic Discipline Project (No. B906).

语种：中文

中文关键词：氯化两面针碱;分子内Heck偶联反应;合成改进

外文关键词：nitidine chloride; intramolecular Heck reaction; synthesis

摘要：以6-溴-3,4-二甲氧基苯甲醛和6,7-亚甲二氧基-1-萘胺为起始原料,经还原胺化、分子内Heck偶联、氧化芳构化、甲基化以及离子交换等五步反应,完成了氯化两面针碱的合成,并对关键步骤分子内Heck偶联反应条件进行了探索,结果表明该偶联反应在醋酸钯、三(邻甲苯基)膦和N,N'-二甲基甲酰胺体系中反应效果最佳,收率显著提高.该优化条件为结构类似苯并[c]菲啶类生物碱母核结构的构建提供了借鉴.
Nitidine chloride was synthesized via reductive amination, intramolecular Heck coupling reaction, aromatization, methlyation and ion exchange, using 6-bromine-3,4-dimethoxybenzaldehyde and 6,7-methylenedioy-1-naphthylamine as starting material. The key intramolecular Heck coupling reaction was optimized, and acetic acid palladium（II） [Pd（OAc）2], tris（2-methylphenyl）phosphine [P（o-tol）3] and N,N-dimethylformamide（DMF） system was confirmed as the most efficient conditions. The total yield was increased significantly, and the optimal conditions may also be applied to the synthesis of other benzo[c]phenanthridine alkaloid.