Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1<i>H</i>-pyrazol-5-amines and 4,5-dihydropyridazin-3(2<i>H</i>)-ones

Chen, Lepeng; Lv, Ningning; Zhen, Qianqian; Chen, Zhongyan; Ge, Jing‐Yuan; Chen, Jiuxi

doi:10.1039/d2qo00036a

Cited by 6 publications

(1 citation statement)

References 38 publications

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“…The authors have cited additional references within the Supporting Information (Ref. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40]).…”

Section: Supporting Informationmentioning

confidence: 99%

Organocatalytic Chemoselective C4‐Benzylation of 5‐Aminopyrazoles

Natarajan,

Kanchithalaivan,

Chatterjee

et al. 2024

Asian J Org Chem

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The first chemoselective C4‐benzylation of 5‐aminopyrazoles, utilizing a 3 mol% squaric acid catalyst, is disclosed. In this process, ortho‐quinone methides are efficiently generated from 2‐hydroxybenzyl alcohols in water under mild conditions. This method successfully delivers a wide range of C4‐benzylated 5‐aminopyrazoles, achieving moderate to excellent yields while demonstrating high chemoselectivity, which is further confirmed by mechanistic studies. Notably, the protocol uses water as an eco‐friendly solvent, requires a low organocatalyst loading, and eliminates the need for column chromatography.

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“…The authors have cited additional references within the Supporting Information (Ref. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40]).…”

Section: Supporting Informationmentioning

confidence: 99%

Organocatalytic Chemoselective C4‐Benzylation of 5‐Aminopyrazoles

Natarajan,

Kanchithalaivan,

Chatterjee

et al. 2024

Asian J Org Chem

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Redox‐Neutral Synthesis of Polycyclic Azaheterocycles via Cobalt‐Catalyzed Hydroarylation/Annulation of Maleimides

Zhou

et al. 2022

Adv Synth Catal

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Unveiling a Novel Mechanistic Pathway: Thiol and DMSO‐Facilitated Synthesis of Pyrazole Amine Thioether

Perumal,

Shanthi,

Hemamalini

et al. 2024

Journal of Heterocyclic Chem

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The present protocol shows a novel and greener approach for synthesizing pyrazole amine thioether, employing thiophenol, 3‐aminocrotononitrile, and phenylhydrazine hydrochloride. Notably, this methodology deviates from the literature report in making thioether derivatives using oxidant‐free and room‐temperature conditions. Based on the control experiments, it was found that the thioether link in the intermediate facilitated the 5‐exo‐dig cyclization reaction exclusively in the DMSO solvent. This is probably due to the nitrile group's activation by the structure's thioether moiety. The control experiment demonstrates the significance of the thioether compound in the reaction. Without any oxidizing agent, introducing thioether in any heterocyclic compound is not possible, as per the literature reports. Our reaction showed excellent tolerance by involving various phenylhydrazine hydrochloride and thiophenol compounds, allowing for the synthesis of various pyrazole amine thioether derivatives in good to excellent yields. The reaction follows the 5‐exo‐dig cyclization strategy.

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Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones

Abstract: Developing efficient methods to accommodate azaheterocycles has been the hotspot field in organic synthesis. Herein, we disclose a facile and expeditious avenue to synthesize 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones via nickel-catalyzed addition,...

Cited by 6 publications

References 38 publications

Organocatalytic Chemoselective C4‐Benzylation of 5‐Aminopyrazoles

Organocatalytic Chemoselective C4‐Benzylation of 5‐Aminopyrazoles

Redox‐Neutral Synthesis of Polycyclic Azaheterocycles via Cobalt‐Catalyzed Hydroarylation/Annulation of Maleimides

Unveiling a Novel Mechanistic Pathway: Thiol and DMSO‐Facilitated Synthesis of Pyrazole Amine Thioether

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