Lewis Acid-Mediated Ring Contraction of 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepines: Access to 2-Aryl-1-styrylbenzimidazoles

被引：0

作者：

Zhang, Mengyao ^{[1
]}

Wu, Qiuyue ^{[1
]}

Xu, Jiaxi ^{[1
]}

机构：

[1] Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, State Key Lab Chem Resource Engn, Beijing 100029, Peoples R China

来源：

HELVETICA CHIMICA ACTA | 2023年 / 106卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Benzimidazoles; benzodiazepines; copper acetate; Lewis acids; ring contraction; CYCLOADDITION REACTION; BENZOHETEROAZEPINE;

D O I：

10.1002/hlca.202200143

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepines readily undergo a ring contraction to generate 2-aryl-1-styrylbenzimidazoles in the presence of some Lewis acids. Copper acetate shows high efficiency compared with other Lewis acids. The ring contraction includes Lewis acid-catalyzed intramolecular addition, ammonium-induced ring-opening of the generated four-membered azetidine ring, deprotonation, and amine-promoted nucleophilic styryl 1,2-shift and elimination. Copper acetate serves as Lewis acid, base, and oxidant. The current reaction provides an efficient method for the convenient synthesis of 2-aryl-1-styrylbenzimidazole derivatives from readily available 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines.

引用

页数：10

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