Synthesis of Quinolinone- and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes

doi:10.6023/cjoc201609027

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 667-674.DOI: 10.6023/cjoc201609027 Previous Articles Next Articles

ARTICLE

喹啉酮和吡啶酮稠合的氧杂双环[3.3.1]壬烷的合成

叶明琰, 邱少中, 殷国栋

湖北师范大学化学化工学院污染物分析与资源化湖北省重点实验室黄石 435002

收稿日期:2016-09-26 修回日期:2016-11-03 发布日期:2016-11-29
通讯作者: 殷国栋,E-mail:gdyin@hbnu.edu.cn,gdyin_hbnu@163.com E-mail:gdyin@hbnu.edu.cn,gdyin_hbnu@163.com
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

Ye Mingyan, Qiu Shaozhong, Yin Guodong

Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002

Received:2016-09-26 Revised:2016-11-03 Published:2016-11-29
Contact: 10.6023/cjoc201609027 E-mail:gdyin@hbnu.edu.cn,gdyin_hbnu@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21542009).

1. Synthesis of Quinolinone- and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes.PDF(28569KB)

Abstract

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.

Key words: 4-hydroxy-2(1H)-quinolinone, 4-hydroxy-2(1H)-pyridinone, bicyclo[3.3.1]nonane, alkylation, X-ray structure

Cite this article

Ye Mingyan, Qiu Shaozhong, Yin Guodong. Synthesis of Quinolinone- and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes[J]. Chin. J. Org. Chem., 2017, 37(3): 667-674.

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喹啉酮和吡啶酮稠合的氧杂双环[3.3.1]壬烷的合成

Synthesis of Quinolinone- and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes

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