[3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture

Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substra...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-01, Vol.366 (2), p.269-276
Main Authors: Li, Yang, Zuo, Wei‐Fang, Chen, Jian‐Hua, Li, Wei, Zheng, Jinfeng, Han, Bo, Li, Xiang, Huang, Wei
Format: Article
Language:English
Subjects:
Amides
Cycloaddition
Enaminone
Pyrazolone
Pyrazolones
Spirocyclic Architecture
Substrates
α-Haloamide
γ-Lactam
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Summary:Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substrate compatibility, and scale‐up capacity. Importantly, this study also represents one of the rare examples that harness enaminone C−N bond cleavage to engineer relevant spirocyclic γ‐lactam skeletons of biological interest. Moreover, we propose a plausible mechanistic explanation to elucidate the outstanding chemical outcomes observed, thereby enriching the synthetic toolbox for pyrazolone chemistry and α‐haloamide‐mediated reactions.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301175