喹啉酮和吡啶酮稠合的氧杂双环[3.3.1]壬烷的合成
收稿日期: 2016-09-26
修回日期: 2016-11-03
网络出版日期: 2016-11-29
基金资助
国家自然科学基金（No.21542009）资助项目.
Synthesis of Quinolinone- and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes
Received date: 2016-09-26
Revised date: 2016-11-03
Online published: 2016-11-29
Supported by
Project supported by the National Natural Science Foundation of China (No. 21542009).
以2-羟基查尔酮与4-羟基-2（1H）-喹啉酮或4-羟基-2（1H）-吡啶酮在正丙醇中回流反应，立体选择性地合成了喹啉酮和吡啶酮稠合的2，8-二氧杂双环[3.3.1]壬烷衍生物.其中，喹啉酮片段通过烷基化反应可转化为相应的氮烷基取代的喹啉酮和氧烷基取代的喹啉结构.目标产物均未见文献报道，其结构都通过了1H NMR、13C NMR、IR和HRMS的表征，6-苯基-2，12-二氢-1H-6，12-亚甲基苯并[7，8][1，3]二氧桥[5，4-c]吡啶-1-酮（3r）和1-异丙氧基-8-苯基-14H-8，14-亚甲基苯并[7，8][1，3]二氧桥[5，4-c]喹啉（6c）的结构和立体构型还进一步获得了X射线单晶衍射的证实.
关键词： 4-羟基-2(1H)-喹啉酮; 4-羟基-2(1H)-吡啶酮; 双环[3.3.1]壬烷; 烷基化; 单晶结构
叶明琰 , 邱少中 , 殷国栋 . 喹啉酮和吡啶酮稠合的氧杂双环[3.3.1]壬烷的合成[J]. 有机化学, 2017 , 37(3) : 667 -674 . DOI: 10.6023/cjoc201609027
An efficient and stereoselective synthesis of quinolinone- and pyridinone-fused 2,8-dioxabicyclo[3.3.1]-nonanes by the reaction of 2-hydroxychalcones with 4-hydroxy-2(1H)-quinolinones/4-hydroxy-2(1H)-pyridinones in refluxing n-PrOH is described. The quinolinone fragment can be converted into the corresponding N-alkylated quinolinones and O-alkylated quinolines by the alkylation reaction. All the unknown compounds are characterized by means of 1H NMR, 13C NMR, IR and HRMS. The structures and configurations of 6-phenyl-2,12-dihydro-1H-6,12-methanobenzo[7,8] [1,3]dioxocino[5,4-c]pyri-din-1-one (3r) and 1-isopropoxy-8-phenyl-14H-8,14-methanobenzo[7,8] [1,3]dioxocino[5,4-c]quinoline (6c) are further confirmed by X-ray single crystal diffraction analysis.
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