[1]刘 斌,田航周,朱周静,等.3-烯丙基-2,4-二氯-6,7-二甲氧基喹啉的合成研究[J].江西师范大学学报(自然科学版),2019,(03):243-247.[doi:10.16357/j.cnki.issn1000-5862.2019.03.05]
 LIU Bin,TIAN Hangzhou,ZHU Zhoujing,et al.The Study on the Synthesis of 3-Allyl-2,4-Dichloro-6,7-Dimethoxyquinoline[J].Journal of Jiangxi Normal University:Natural Science Edition,2019,(03):243-247.[doi:10.16357/j.cnki.issn1000-5862.2019.03.05]
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3-烯丙基-2,4-二氯-6,7-二甲氧基喹啉的合成研究()
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《江西师范大学学报》(自然科学版)[ISSN:1006-6977/CN:61-1281/TN]

卷:
期数:
2019年03期
页码:
243-247
栏目:
化学与生命科学
出版日期:
2019-06-10

文章信息/Info

Title:
The Study on the Synthesis of 3-Allyl-2,4-Dichloro-6,7-Dimethoxyquinoline
文章编号:
1000-5862(2019)03-0243-05
作者:
刘 斌12田航周1朱周静1丁芳芳1左振宇23
1.陕西国际商贸学院医药学院,陕西 西安 712046; 2.陕西省中药绿色制造技术协同创新中心,陕西 西安 712046; 3.陕西中医药大学药学院,陕西 西安 712046
Author(s):
LIU Bin12TIAN Hangzhou1ZHU Zhoujing1DING Fangfang1ZUO Zhenyu23
1.School of Pharmacy,Shaanxi Institute of International Trade and Commerce,Xi'an Shaanxi 712046,China; 2.Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province,Xi'an Shaanxi 712046,China; 3.College of Pharmacy,Shanxi University of Chinese Medicine,Xi'an Shaanxi 712046,China
关键词:
喹啉衍生物 24-二氯-67-二甲氧基喹啉 合成 应用
Keywords:
quinoline derivatives 24-dichloro-67-dimethoxyquinoline synthesis application
分类号:
TQ 463
DOI:
10.16357/j.cnki.issn1000-5862.2019.03.05
文献标志码:
A
摘要:
以3,4-二甲氧基苯胺和丙二酸为原料,在三氯氧磷作用下合成2,4-二氯-6,7-二甲氧基喹啉,2,4-二氯-6,7-二甲氧基喹啉在二异丙基氨基锂作用下与3-溴丙烯发生SNAr反应得到3-烯丙基-2,4-二氯-6,7-二甲氧基喹啉.2步反应总收率为66.1%.产物结构经1H NMR和ESI-MS确证.通过对反应条件研究确定最佳反应工艺,在该最佳反应工艺条件下2,4-二氯-6,7-二甲氧基-3-(2-甲基烯丙基)喹啉的合成收率为77.5%.3-烯丙基-2,4-二氯-6,7-二甲氧基喹啉经过还原、氧化、取代反应得到3-(3-叔丁基二甲基硅氧丙基)-2,4-二氯-6,7-二甲氧基喹啉,3步反应总收率为42.8%.
Abstract:
3-Allyl-2,4-dichloro-6,7-dimethoxyquinoline is synthesized by an efficient and practical method from 3,4-dimethoxyaniline and malonic acid,through two steps in a total yield of 66.1%,involving 2,4-dichloro-6,7-dimethoxyquinoline forming in the presence of POCl3,then SNAr reaction of 2,4-dichloro-6,7-dimethoxyquinoline with 3-bromoprop-1-ene in the presence of lithium diisopropylamide.The structure of the intermediate and product are confirmed by 1H NMR and ESI-MS.The optimal reaction conditions are investigated.Also,2,4-dichloro-6,7-dimethoxy-3-(2-methylallyl)quinoline is obtained by the optimal reaction process in a yield of 77.5%.The synthetic application of 3-allyl-2,4-dichloro-6,7-dimethoxyquinoline is also investigated.3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2,4-dichloro-6,7-dimethoxyquinoline is synthesized in a yield of 42.8% from title compound through reduction,oxidation and substitution reaction.

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备注/Memo

备注/Memo:
收稿日期:2018-10-08
基金项目:陕西省自然科学基金(2018JM7046)和陕西国际商贸学院“中药药物研究”创新团队(SSY18TD01)资助项目.
作者简介:刘 斌(1982-),男,陕西渭南人,讲师,博士,主要从事药物分子设计合成研究.E-mail:lb125lb@163.com
更新日期/Last Update: 2019-06-10