Synthesis of difluoromethylated spiropyrazolones [3 + 2] cycloaddition of difluoroacetohydrazonoyl bromides with alkylidene pyrazolones

An effective [3 + 2] cycloaddition reaction of difluoromethyl or trifluoromethyl hydrazonoyl bromides with alkylidene pyrazolones was disclosed. This method provides an efficient approach for accessing a variety of highly functionalized fluoroalkyl spiropyrazolones in good yields. This protocol also...

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Published in:Organic & biomolecular chemistry 2024-04, Vol.22 (14), p.2797-2812
Main Authors: Feng, Yang, Ren, Yuanyuan, Tang, Duoduo, Wang, Ke-Hu, Wang, Junjiao, Huang, Danfeng, Lv, Xiaobo, Hu, Yulai
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Summary:An effective [3 + 2] cycloaddition reaction of difluoromethyl or trifluoromethyl hydrazonoyl bromides with alkylidene pyrazolones was disclosed. This method provides an efficient approach for accessing a variety of highly functionalized fluoroalkyl spiropyrazolones in good yields. This protocol also features some advantages such as easily available and stable substrates, simple operation procedures, and atom and step economy. The formation of ( cis )- and ( trans )-products was discussed. Highly functionalized fluoroalkyl spiropyrazolones are synthesized via an effective [3 + 2] cycloaddition of di/trifluoromethyl hydrazonoyl bromides and alkylidene pyrazolones in good yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00044g