Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C-N or C-C Azirine Bond in 2-Pyridylazirines

被引：4
|
作者：
Agafonova, Anastasiya V. [1 ]
Golubev, Artem A. [1 ]
Smetanin, Ilia A. [1 ]
Khlebnikov, Alexander F. [1 ]
Spiridonova, Dar'ya V. [1 ]
Novikov, Mikhail S. [1 ]
机构：
[1] St Petersburg State Univ, Inst Chem, St Petersburg 199034, Russia
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 39期
基金：
俄罗斯科学基金会;
关键词：
BIOLOGICAL EVALUATION; FLUORESCENT-PROBE; DERIVATIVES; DESIGN;
D O I：
10.1021/acs.orglett.3c02696
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The three-membered ring in 2-(2-pyridyl)azirine-2-carboxylic esters and thioesters can undergo selective cleavage of either the N-C2 bond under copper(II) catalysis or the C-C bond under the action of HCl to provide isomeric azirine ring expansion products of pyrazolo[1,5-a]pyridine or imidazo[1,5-a]pyridine series, respectively. Mild catalytic reaction conditions for the formation of pyrazolopyridines make it possible to obtain them directly from 4-bromoisoxazoles by a one-pot, three-stage procedure without isolating the intermediate 2-bromoazirines and 2-(2-pyridyl)azirines.
引用
收藏
页码：7165 / 7169
页数：5
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