Synthesis of Fused Polycyclic 1,4-Benzodiazepines via Metal-Free Cascade [5+2]/[2+2] Cycloadditions

被引：45
|
作者：
Shin, Jinhwan [1 ]
Lee, Jiyoun [1 ]
Ko, Donguk [1 ]
De, Nirupam [1 ]
Yoo, Eun Jeong [1 ]
机构：
[1] Kangwon Natl Univ, Dept Chem, 1 Kangwondaehak Gil, Chunchon 24341, South Korea
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 11期
基金：
新加坡国家研究基金会;
关键词：
BENZYNE CLICK CHEMISTRY; DIELS-ALDER REACTIONS; EFFICIENT SYNTHESIS; CIRCUMDATIN-F; ARYNES; REACTIVITY; BENZODIAZEPINES; BRETAZENIL; AGONIST; ACCESS;
D O I：
10.1021/acs.orglett.7b01137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-catalyst-free, mild, and efficient synthetic protocol for polycyclic 1,4-benzodiazepines via cascade [5 + 2]/[2 + 2] cycloadditions between pyridinium zwitterions and arynes is reported. Mechanistic experiments revealed that pyridinium zwitterions act as 1,5-dipoles in [5 + 2] cycloadditions with arynes for the construction of 1,4-benzodiazepines, which further undergo [2 + 2] cycloaddition resulting in the one-pot formation of one CN bond and three CC bonds.
引用
收藏
页码：2901 / 2904
页数：4
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