【摘要】 以脱氢松香酸甲酯(Ⅱ)为起始原料,通过在12位溴代得到12-溴-脱氢松香酸甲酯(Ⅲ),再经过在13位选择性硝化后还原制得中间体13-氨基脱异丙基脱氢松香酸甲酯(Ⅴ),Ⅴ继续与甘油在浓硫酸作用下缩合得(4R,12bS)-4,12b-二甲基-1,2,3,4,4a,5,6,12b-八氢化萘并[1,2-g]喹啉-4-羧酸甲酯(Ⅵ)和(7R,10aS)-7,10a-二甲基-5,6,6a,7,8,9,10,10a-八氢化萘并[2,1-f]喹啉-7-羧酸甲酯(Ⅶ)两种松香基喹啉衍生物,这两种产物的产率分别为51.2%和20.3%,质量分数分别为71.6%和28.4%,产物的结构通过IR,1HNMR和元素分析进行了表征。更多还原

【Abstract】 Two quinoline derivatives from dehydroabietic acid were synthesized.Methyl dehydroabietate(Ⅱ)was bromated at 12-position to give methyl 12-bromo-dehydroabiete(Ⅲ).From Ⅲ,methyl 13-aminodeisopropyldehydroabietate(Ⅴ)was synthesized by nitration with nitric acid and hydrogenation in the presence of H2 and Pd/C.Then Ⅴ was further converted into two quinoline derivatives,namely methyl(4R,12bS)-4,12b-dimethyl-1,2,3,4,4a,5,6,12b-octahydronaphtho [1,2-g] quinoline-4-carboxylate(Ⅵ)and methyl(7R,10aS)-7,10a-dimethyl-5,6,6a,7,8,9,10,10a-octahydronaphtho [2,1-f] quinoline-7-carboxylate(Ⅶ),by condensation with glycerol in the presence of concentrated sulfuric acid.The yields were 51.2 % and 20.3 %,and the mass fraction were 71.6 % and 28.4 %,respectively.Their structurs were characterized by IR,1H NMR and elemental analysis.更多还原