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,Organic Letters

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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
Organic Letters ( IF 4.9 ) Pub Date : 2023-09-22 , DOI: 10.1021/acs.orglett.3c02696
Anastasiya V Agafonova ₁ , Artem A Golubev ₁ , Ilia A Smetanin ₁ , Alexander F Khlebnikov ₁ , Dar'ya V Spiridonova ₁ , Mikhail S Novikov ₁

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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.

中文翻译：

通过试剂控制 2-吡啶基氮丙啶中 C-N 或 C-C 氮丙啶键的断裂合成吡唑并[1,5-a]吡啶和咪唑并[1,5-a]吡啶

2-(2-吡啶基)氮丙啶-2-羧酸酯和硫酯中的三元环可以在铜(II)催化下选择性裂解N-C2键或在HCl作用下选择性裂解C-C键，分别提供吡唑并[1,5- a ]吡啶或咪唑并[1,5- a ]吡啶系列的异构氮丙啶扩环产物。形成吡唑并吡啶的温和催化反应条件使得可以通过一锅、三阶段程序直接从4-溴异恶唑获得它们，而无需分离中间体2-溴氮丙啶和2-(2-吡啶基)氮丙啶。

更新日期：2023-09-22

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