Regioselective Synthesis of Pyrazolo[1,5-a]pyridine via TEMPO-Mediated [3+2] Annulation-Aromatization of N-Aminopyridines and α,β-Unsaturated Compounds

被引：22

作者：

Wang, Amu ^{[1
,2
]}

Liu, Ya-Zhou ^{[1
]}

Shen, Zhongke ^{[1
,2
]}

Qiao, Zeen ^{[1
]}

Ma, Xiaofeng ^{[1
]}

机构：

[1] Chinese Acad Sci, Nat Prod Res Ctr, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 07期

基金：

中国国家自然科学基金;

关键词：

CYCLOADDITION; DISCOVERY; EFFICIENT; IMIDES;

D O I：

10.1021/acs.orglett.2c00035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A TEMPO-mediated [3 + 2] annulation-aromatization protocol for the preparation of pyrazolo[1,5-a]pyridines from N-aminopyridines and alpha,beta-unsaturated compounds was developed. The procedure offered multisubstituted pyrazolo[1,5a]pyridines in good to excellent yield with high and predictable regioselectivity. The modification of marketed drugs including Loratadine, Abiraterone, and Metochalcone, and a one-pot threestep gram scale synthesis of key intermediate for the preparation of Selpercatinib were demonstrated. Mechanism studies show that TEMPO serves both as a Lewis acid and as an oxidant.

引用

页码：1454 / 1459

页数：6

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