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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