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

页码：7165 / 7169

页数：5

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