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

页码：2901 / 2904

页数：4

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