Synthesis of 4,5-Dihydropyrazoles via Palladium-Catalyzed Cyclization Reactions of β,γ-Unsaturated Hydrazones with Aryl Iodides

Ding, Rongcai; Lu, Rongmei; Fang, Zixuan; Liu, Yanjun; Wang, Shaoyu; Liang, Xiaoxia; Zhang, Cheng; Huang, Tianyi; Hu, Jinxing

doi:10.1021/acs.organomet.9b00656

Organometallics

2019

DOI: 10.1021/acs.organomet.9b00656

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Synthesis of 4,5-Dihydropyrazoles via Palladium-Catalyzed Cyclization Reactions of β,γ-Unsaturated Hydrazones with Aryl Iodides

Rongcai Ding

Rongmei Lu

Zixuan Fang

et al.

Abstract: A novel two-component cyclization toward the synthesis of polysubstituted 4,5-dihydropyrazoles was carried out: i.e., cyclization of β,γ-unsaturated hydrazones with aryl iodides catalyzed by Pd(0). The reaction forms new carbon− carbon bonds and carbon−nitrogen bonds with moderate to good reactivity.

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Cited by 8 publications

References 22 publications

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Update on the Synthesis of N‐Heterocycles via Cyclization of Hydrazones (2017–2021)

Meng

et al. 2021

Adv Synth Catal

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Hydrazones, as universal structural units, are useful synthons for the formation of carbonnitrogen and nitrogenÀ heteroatom bonds. Thus, they provide new methods of constructing nitrogen-containing heterocycles. In recent years, especially between 2017 and 2021, many efforts have been made to exploit hydrazone-based reactions in efforts to develop more powerful and effective pathways towards the synthesis of various multifunctional heterocyclic compounds. However, despite the tremendous amount of work that has been published over the past five years, no review has been published that summarizes the significant progress in the preparation of nitrogen heterocycles via intramolecular cyclization of hydrazones with adjacent unsaturated bonds or intermolecular cyclization of hydrazones with unsaturated systems. Therefore, this review summarizes the hydrazone-based cyclization strategies used to synthesize nitrogen-containing heterocycles over the past five years. It discusses the corresponding reaction scopes, limitations, mechanisms, and problems. Cyclization of Hydrazones with Unsaturated Systems 3.3. Cyclization of Hydrazones with Unsaturated Systems Under Metal-Free Conditions 4. Conclusion

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Update on the Synthesis of N‐Heterocycles via Cyclization of Hydrazones (2017–2021)

Meng

et al. 2021

Adv Synth Catal

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Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives

Jovanovic,

Petkovic

et al. 2024

Adv Synth Catal

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Combining chemical reactivities of allenes and oximes created a methodology for the preparation of heterocyclic triquinane‐type skeletons via a cascade process constructing four bonds in a single step. The initial reaction of allene moiety promoted by Pd‐catalysis, affording π‐allyl Pd‐species, was followed by two additional transformations ‐ nucleophilic displacement and dipolar cycloaddition ‐ to furnish the product highly stereoselectively in moderate to good yields. For the process to be efficient, it was necessary to use a dipolarophilic component as a solvent. Intriguingly, while the reaction with cyclopentanone derived oxime progressed through the whole cascade, with cyclohexanone analogue it stopped at the nitrone stage, requiring an additional step to yield similar type of products. Some aspects of the studied cascade were examined by DFT.

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Waste minimized one-pot synthesis of azido- or triazole-pyrazolines using polarclean as reaction medium

Campana,

Maselli,

Falcini

et al. 2024

Sustainable Chemistry and Pharmacy

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Synthesis of 4,5-Dihydropyrazoles via Palladium-Catalyzed Cyclization Reactions of β,γ-Unsaturated Hydrazones with Aryl Iodides

Cited by 8 publications

References 22 publications

Update on the Synthesis of N‐Heterocycles via Cyclization of Hydrazones (2017–2021)

Update on the Synthesis of N‐Heterocycles via Cyclization of Hydrazones (2017–2021)

Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives

Waste minimized one-pot synthesis of azido- or triazole-pyrazolines using polarclean as reaction medium

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