Tunable Synthesis of 3-Acyl-2-naphthols and 3-Substituted Isocoumarins via Jones Reagent Promoted Cascade Reactions of 2-(4-Hydroxy-but-1-ynyl)benzaldehydes

被引：23
|
作者：
He, Yan [1 ,2 ]
Zhang, Xinying [2 ]
Shen, Nana [2 ]
Fan, Xuesen [1 ,2 ]
机构：
[1] Henan Normal Univ, Sch Environm, Key Lab Yellow River & Huai River Water Environm, Minist Educ, Xinxiang 453007, Henan, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Key Lab Green Chem Media & React, Minist Educ, Xinxiang 453007, Henan, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 20期
关键词：
CYCLIZATION; INHIBITORS; ACID; DERIVATIVES; REARRANGEMENT; ACYLATION; PHENOLS;
D O I：
10.1021/jo401502k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel and efficient synthesis of 3-acyl-2- 1) naphthols and 3-substituted isocoumarins via the tunable cascade reactions of 2-(4-hydroxy-but-1-ynyl)benzaldehydes have been developed. Treatment of 2-(4-hydroxy-but-1-ynyl)benzaldehydes with 0.7 equiv of Jones reagent in CH3CN and subsequent purification through column chromatography on silica gel pre-eluted with Et3N afforded 3-acyl-2-naphthols with high efficiency. When the same substrates were treated with 3 equiv of Jones reagents in acetone, on the other hand, 3-substituted isocoumarins could be obtained in good yields.
引用
收藏
页码：10178 / 10191
页数：14
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