摘要
以奎宁为原料,经羟基氧化、开环、氨基Boc保护、双键臭氧氧化、醛基还原、羟基甲磺酰化后叠氮取代、叠氮基团的氢化还原及分子内环合等9步反应,合成了一种新的萘啶衍生物,即标题化合物。对其中关键的双键臭氧氧化和分子内环合的反应条件进行了研究,确定了较佳反应条件:双键臭氧氧化反应在-78℃下以臭氧为氧化剂、乙酸乙酯为溶剂;分子内环合反应以甲醇钠为碱、甲醇为溶剂,在65℃条件下反应12 h。中间体及目标化合物的结构均经核磁共振氢谱、碳谱、质谱和元素分析进行确定。
2-Boc-6-oxo-octahydro [2,7] naphthyridine was synthesized from quinine by the reactions of oxidation,ring-opening,protection of amine,oxidation of double bond with ozone,reduction of aldehyde,mesylation of hydroxyl group and then azidation by sodium azide,hydrogenation reduction of azide group and intramolecular cyclization. The optimum conditions of oxidation of double bond and intramolecular cyclization were obtained. For oxidation of double bond,-78 ℃,O3 as the oxidant,ethyl acetate as solvent. For intramolecular cyclization,sodium methylate as a base,refluxing in methanol for 12 h. The structures of intermediates and target product were confirmed by ^1HNMR,^13CNMR,MS and elemental analysis.
出处
《化学试剂》
北大核心
2017年第5期553-557,共5页
Chemical Reagents
基金
山东省高校科技计划资助项目(J16LC13)
