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Updated: Oct 25, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Cascade Spirocyclization-Difunctionalization or Rearrangement of Bicyclobutyl-Tethered Aldehyde Hydrazones via Strain
Haiyang Sun1, Lijun Li1, Qinqin Yan1
1State Key Laboratory of New Pharmaceutical Preparations and Excipients, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Materials Science, Hebei University, Baoding, Hebei071002, China.
Abstract:
A cascade spirocyclization-difunctionalization of bicyclobutyl-tethered aldehyde hydrazones with N-halosuccinimides was smoothly performed to access diverse halo-succinimide-containing diazaspiro[3.3]heptan-3-ones. Meanwhile, the three-component rearrangement of bicyclobutyl-tethered aldehyde hydrazones, N-halosuccinimides, and NH-sulfoximines also proceeded under similar conditions to give various halo-sulfoximine-featured phenyldiazenyl cyclobutane-1-carboxamides. In addition, some scaled-up experiments and complex substrates were explored in system application studies. Finally, a plausible reaction process was proposed according to mechanistic studies.
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