含氟双环吡啶类杂环化合物的“一步法”合成有机化学.pdfVIP

DOI: 10.6023/cjoc201503019 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 含氟双环吡啶类杂环化合物的“一步法”合成 彭美阳†,a 杨瑞霞†,a 刘昔敏a 严胜骄*,a 林 军*,a,b (a 云南大学化学科学与工程学院 教育部自然资源药物化学重点实验室 昆明 650091) (b 云南大学现代分析测试中心 昆明 650091) 摘要 建立了以杂环烯酮缩胺为原料与含氟β-二羰基化合物在酸性条件下“一步法”合成含氟双环吡啶类化合物的方 法. 以含氟β-二羰基化合物三氟乙酰乙酸乙酯(2) 、六氟乙酰丙酮(3)为砌块在 1,4-二氧六环溶剂中, 醋酸催化下分别与 杂环烯酮缩胺 1 反应, “一步法”简捷高效地合成了一系列新的含氟双环吡啶类化合物 4a～4e 及 5a～5e, 产率 79%～ 95%. 该方法具有原料易得、合成路线简捷、产率高、后处理简单等优点. 关键词 含氟; 双环吡啶; 杂环化合物; 醋酸 One Step Synthesis of Fluorine-Containing Bicyclicpyridine Compounds Peng, Meiyang†,a Yang, Ruixia†,a Liu, Ximina Yan, Shengjiao*,a Lin, Jun*,a,b a ( Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091) b ( Modern Analytical Test Center, Yunnan University, Kunming 650091) Abstract In this work, one step synthesis of fluorine-containing bicyclic pyridine heterocyclic compounds protocol was es- tablished. This method based on the building blocks of β-dicarbonyl compound ethyl 4,4,4-trifluoro-3-oxobutanoate (2) or hexafluoropentane-2,4-dione (3), which reacted with heterocyclic ketene aminals 1 respectively under acetic acid as catalyst and 1,4-dioxane as the solvent. As a result, a series of new fluorinated pyridine compounds 4a～4e and 5a～5e have been