8-羟基异香豆素的合成方法研究
收稿日期: 2019-06-03
修回日期: 2019-07-22
网络出版日期: 2019-08-07
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
Received date: 2019-06-03
Revised date: 2019-07-22
Online published: 2019-08-07
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).
郭冬冬 , 张武霞 , 王永强 . 8-羟基异香豆素的合成方法研究[J]. 有机化学, 2019 , 39(9) : 2650 -2654 . DOI: 10.6023/cjoc201906001
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
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