The Practical Access to Fluoroalkylated Pyrazolo[1,5- c]quinazolines by Fluoroalkyl-Promoted [3 + 2] Cycloaddition Reaction

Liu-Yan Qiu; Nan Ren; Zhen Deng; Jie Chen; Hongmei Deng; Hui Zhang; Weiguo Cao; Xiao-Jun Tang

doi:10.1021/acs.joc.3c00025

The Practical Access to Fluoroalkylated Pyrazolo[1,5- c]quinazolines by Fluoroalkyl-Promoted [3 + 2] Cycloaddition Reaction

J Org Chem. 2023 Jul 21;88(14):10180-10189. doi: 10.1021/acs.joc.3c00025. Epub 2023 Jul 6.

Authors

Liu-Yan Qiu¹, Nan Ren¹, Zhen Deng¹, Jie Chen¹, Hongmei Deng², Hui Zhang², Weiguo Cao^{1

3}, Xiao-Jun Tang¹

Affiliations

¹ Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China.
² Laboratory for Microstructures and Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, China.
³ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 37410945
DOI: 10.1021/acs.joc.3c00025

Abstract

The efficient synthesis of fluoroalkylated pyrazolo[1,5-c]quinazolines by reactions of 3-diazoindolin-2-ones with methyl β-fluoroalkylpropionates has been achieved. This protocol affords two regioisomers of fluoroalkylated pyrazolo[1,5-c]quinazolines with excellent yields in total. The dipolarophilicity of methyl β-fluoroalkylpropionates enhanced by perfluoroalkyl groups is crucial for the high efficiency of this [3 + 2] cycloaddition reaction.