Study on Synthetic Approach to 8-Hydroxyisocoumarin

doi:10.6023/cjoc201906001

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2650-2654.DOI: 10.6023/cjoc201906001 Previous Articles Next Articles

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8-羟基异香豆素的合成方法研究

郭冬冬^a, 张武霞^a, 王永强^b

a 山西农业大学文理学院山西太谷 030801;
b 西北大学化学与材料科学学院西安 710069

收稿日期:2019-06-03 修回日期:2019-07-22 发布日期:2019-08-07
通讯作者: 王永强 E-mail:wangyq@nwu.edu.cn
基金资助:
国家自然科学基金（No.31800678）、山西省优秀博士来晋工作奖励（No.SXYBKY201737）和山西农业大学科技创新基金（No.2017YJ38）资助项目.

Study on Synthetic Approach to 8-Hydroxyisocoumarin

Guo Dongdong^a, Zhang Wuxia^a, Wang Yongqiang^b

a College of Arts and Sciences, Shanxi Agricultural University, Taigu, Shanxi 030801;
b Department of Chemistry & Materials Science, Northwest University, Xi'an 710069

Received:2019-06-03 Revised:2019-07-22 Published:2019-08-07
Contact: 10.6023/cjoc201906001 E-mail:wangyq@nwu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31800678), the Shanxi Excellent Doctor Grant Award (No. SXYBKY201737) and the Science and Technology Innovation Project of Shanxi Agricultural University (No. 2017YJ38).

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Abstract

A new method for the synthesis of 8-hydroxyisocoumarin is reported. 8-Hydroxyisocoumarin was synthesized from Meldrum's acid by Friedel-Crafts acylation, carbonyl protection, ester reduction and deprotection. The key intermediate 3-ethynyl-2-(hydroxymethyl)cyclohex-2-en-1-one was synthesized by acidic cycloaddition, aromatization of cyclohexanone ring and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) oxidation. The structures were characterized by ¹H NMR, ¹³C NMR, IR, and HRMS.

Key words: isocoumarin, 8-hydroxyisocoumarin, pyran, aromatization, synthetic method

Cite this article

Guo Dongdong, Zhang Wuxia, Wang Yongqiang. Study on Synthetic Approach to 8-Hydroxyisocoumarin[J]. Chin. J. Org. Chem., 2019, 39(9): 2650-2654.

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8-羟基异香豆素的合成方法研究

Study on Synthetic Approach to 8-Hydroxyisocoumarin

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