文献类型：期刊文献

中文题名：3-(1,4-二氮杂双环[3.2.2]壬烷基)-5,5-二氧-6-氨基二苯并噻吩的合成工艺改进

英文题名：Improvement of synthesis process of 3-(1,4-diazabicyclo[3.2.2]nonyl)-5,5-dioxo-6-aminodibenzothiophene

作者：杨涛[1];吴君臣[1]

机构：[1]华东理工大学化学与分子工程学院,上海200237

年份：2020

卷号：15

期号：12

起止页码：1386

中文期刊名：中国科技论文

外文期刊名：China Sciencepaper

收录：北大核心:【北大核心2017】；

基金：国家自然科学基金资助项目(21778017)。

语种：中文

中文关键词：3-(1,4-二氮杂双环3.2.2壬烷基)-5,5-二氧-6-氨基二苯并噻吩;硝化试剂;催化剂;乌尔曼偶联反应

外文关键词：3-(1,4-diazabicyclo[3.2.2]nonyl)-5,5-dioxo-6-aminodibenzothiophene;nitrating agent;catalyst;Ullman coupling reaction

摘要：找到一种安全可靠的合成3-(1,4-二氮杂双环[3.2.2]壬烷基)-5,5-二氧-6-氨基二苯并噻吩方法,对化合物3-(1,4-二氮杂双环[3.2.2]壬烷基)-5,5-二氧-6-氨基二苯并噻吩原有的合成路线进行了优化改进,设计出操作更加简单、毒性较小且安全可靠的合成路线。对化合物4-硝基二苯并噻吩的反应条件进行了改进,选用价格低廉的九水合硝酸铁作为硝化试剂;选用甲苯作为溶剂,降低了反应毒性,并且发现当反应温度在100℃时产率最高。合成3-(1,4-二氮杂双环[3.2.2]壬烷基)-5,5-二氧-6-氨基二苯并噻吩时,用L-脯氨酸、CuI作为催化剂,进行乌尔曼偶联反应,该步反应操作容易,反应条件较为温和。
A safe and reliable synthetic method for 3-(1,4-diazabicyclo[3.2.2]nonyl)-5,5-dioxo-6-aminodibenzothiophene was found.The original synthetic route for compound 3-(1,4-Diazabicyclo[3.2.2]nonyl)-5,5-dioxo-6-aminodibenzothiophene was optimized and improved.Synthetic route that is simpler,less toxic and safer was designed.In order to reduce the production price,cheap iron nitrate nonahydrate was selected as the nitrating agent.Toluene was used as solvent reduces toxicity during reaction.And it was found that the yield was highest when the reaction temperature was 100℃.Using L-proline and CuI as catalysts,Ullman coupling reaction was performed to synthesize 3-(1,4-diazabicyclo[3.2.2]nonyl)-5,5-dioxo-6-nitrodibenzothiophene.This step is easy to operate and the reaction conditions are mild.