Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dinner and 1,3-Dicarbonyl Compounds

被引：32

作者：

Huang, Wenbo ^{[1
]}

Xu, Jing ^{[1
]}

Liu, Changhui ^{[1
]}

Chen, Zhiyan ^{[1
]}

Gu, Yanlong ^{[1
,2
]}

机构：

[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Key Lab Large Format Battery Mat & Syst, Minist Educ, Wuhan 430074, Hubei, Peoples R China

[2] Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 05期

基金：

中国国家自然科学基金;

关键词：

CYCLIZATION; ANNULATION;

D O I：

10.1021/acs.joc.9b00270

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzoffirans.

引用

页码：2941 / 2950

页数：10

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