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.
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页数：10
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