Oxidative Annulation of Aldehydes, 5‐Aminopyrazoles, and Nitriles: Synthesis and Applications of Pyrazolo[3,4‐d]Pyrimidines

Author:

Yao Guangkai1,Zhu Chuanle2ORCID,Qin Tianyi1,Wang Mengfan1,Sun Zhixiu1,Tang Ri‐Yuan1ORCID,Zhao Chen1,Jiang Huanfeng2ORCID,Xu Hanhong1ORCID

Affiliation:

1. Key Laboratory of Natural Pesticide and Chemical Biology Ministry of Education South China Agricultural University 510642 Guangzhou People's Republic of China

2. Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology 510640 Guangzhou People's Republic of China

Abstract

AbstractThe oxidative [3+2+1] annulation reaction of aldehydes, 5‐aminopyrazoles, and nitriles is achieved under the oxidation of I2/O2, affording various valuable pyrazolo[3,4‐d]pyrimidines in 27%–91% yields. The salient feature of this reaction is transition‐metal free, operationally simple, broad substrate scope, good functional group tolerance, and gram‐scalable. Remarkably, the corresponding products exhibited intriguing photophysical properties such as Aggregation‐Induced Emission (AIE) and intramolecular charge transfer (ICT) and showed good potential to specifically light up lipid droplets (LDs) in living cells with bright fluorescence, low cytotoxicity, and good photostability.magnified image

Funder

National Natural Science Foundation of China

Basic and Applied Basic Research Foundation of Guangdong Province

China Postdoctoral Science Foundation

Publisher

Wiley

Subject

General Chemistry

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