3-烯丙基-2,4-二氯-6,7-二甲氧基喹啉的合成研究
The Study on the Synthesis of 3-Allyl-2,4-Dichloro-6,7-Dimethoxyquinoline

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%.
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