Synthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols

被引：24

作者：

Rehan, Mohammad ^{[1
]}

Nallagonda, Rajender ^{[1
]}

Das, Braja Gopal ^{[1
]}

Meena, Tannu ^{[1
]}

Ghorai, Prasanta ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 07期

关键词：

ONE-POT SYNTHESIS; ASSISTED INTRAMOLECULAR AMINATION; PALLADIUM-CATALYZED SYNTHESIS; UNACTIVATED INTERNAL ALKYNES; METAL-FREE SYNTHESIS; IN-VITRO EVALUATION; ALLYLIC ALCOHOLS; C-H; BENZOFURAN DERIVATIVES; 2,3-DISUBSTITUTED BENZOFURANS;

D O I：

10.1021/acs.joc.6b02752

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Disclosed herein is an efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans via a regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cirinamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcohols catalyzed by Re2O7, followed by an oxidative cyclization using the above Pd catalyst, is performed. The reaction showed broad substrate scope with good to excellent yields.

引用

页码：3411 / 3424

页数：14

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