Novel Synthesis of 3-Aryl-4-hydroxybenzofurans via Four-Component Reaction from Substituted Nitrostyrenes, Aromatic Aldehydes, Cyclohexan-1,3-diones, and Ammonium Acetate

被引：5

作者：

Li, Yan ^{[1
]}

Liu, Hui ^{[1
]}

Sun, Liang ^{[2
]}

Liu, Juanjuan ^{[1
]}

Xue, Zhiheng ^{[1
]}

Yao, Juan ^{[1
]}

Wang, Cunde ^{[1
]}

机构：

[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225002, Peoples R China

[2] Yancheng Orgun Pharmaceut Sci & Tech Co Ltd, Yancheng 224400, Peoples R China

来源：

SYNLETT | 2013年 / 24卷 / 14期

基金：

中国国家自然科学基金;

关键词：

multicomponent reaction; 4-hydroxybenzofuran; substituted beta-nitrostyrene; dehydroaromatization; cyclohexane-1,3-dione; 5-MEMBERED RING-SYSTEMS; SOLID-PHASE SYNTHESIS; BENZOFURAN; INHIBITORS; ORGANOCATALYSTS; NITROOLEFINS; CONSTRUCTION; HETEROCYCLES; SERIES; FURANS;

D O I：

10.1055/s-0033-1339332

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An one-pot-reaction methodology was developed to synthesize a variety of polysubstituted 3-aryl-2-arylmethylene amino-4-hydroxybenzofurans from substituted beta-nitrostyrenes, aromatic aldehydes, ammonium acetate, and cyclohexane-1,3-diones for the generation of a wide range of structurally interesting and pharmacologically significant compounds. The reaction pathway involves Michael addition of substituted nitrostyrenes and cyclohexane-1,3-diones, then nucleophilic addition of 2-(2-nitro-1-phenylethyl) cyclohexane-1,3-dione and Schiff base generated from aromatic aldehyde and ammonium acetate and intramolecular cyclization, followed by dehydroaromatization to afford the corresponding 3-aryl-2-arylmethyleneamino-4-hydroxybenzofurans.

引用

页码：1851 / 1855

页数：5

共 31 条

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