Tandem Addition/Cyclization/Halogenation Reaction of Difluoromethylated N‑Acylhydrazones with Allyltrimethylsilanes

As novel difluoromethyl building blocks, difluoromethylated N-acylhydrazones react with allyltrimethylsilanes and the halogen source via a tandem addition/cyclization/halogenation strategy, which produces various difluoromethylpyrazoline compounds in good yields. The method features mild reaction co...

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Veröffentlicht in:Journal of organic chemistry 2023-12, Vol.88 (24), p.17356-17367
Hauptverfasser: Zhou, Yuxiu, Ma, Ransong, Li, Xiaoyong, Liu, Xiaokang, Wang, Ke-Hu, Wang, Junjiao, Huang, Danfeng, Hu, Yulai
Format: Artikel
Sprache:eng
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Zusammenfassung:As novel difluoromethyl building blocks, difluoromethylated N-acylhydrazones react with allyltrimethylsilanes and the halogen source via a tandem addition/cyclization/halogenation strategy, which produces various difluoromethylpyrazoline compounds in good yields. The method features mild reaction conditions, broad substrate scopes, and a transition metal-free process with easy operation. It also proves that difluoromethylated N-acylhydrazones are useful difluoromethyl building blocks for the construction of difluoromethylated nitrogen heterocycles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02174