Synthesis of spirocyclopropylpyrazole derivatives <i>via</i> the cascade reaction of alkylidenecyclopropanes with pyrazolidinones and trifluoroethanol

Shen, Mohai; Xu, Yu; Zhang, Xinying; Fan, Xuesen

doi:10.1039/d1qo01921j

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2024

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Cited by 7 publications

(1 citation statement)

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“…48 On the other hand, spirocyclic skeletons containing three- and four-membered rings also deserve more attention from chemists working in related areas. 49 Hopefully, this review will be useful to researchers working in organic and medicinal chemistry and to stimulate enthusiasm to make more efforts for future development.…”

Section: Discussionmentioning

confidence: 99%

C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds

Zhou,

Li,

Zhang

et al. 2024

Org. Biomol. Chem.

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Section: Discussionmentioning

confidence: 99%

C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds

Zhou,

Li,

Zhang

et al. 2024

Org. Biomol. Chem.

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Catalytic Asymmetric Syntheses of Alkylidenecyclopropanes from Allenoates with Donor‐Acceptor and Diacceptor Diazo Reagents

Hasegawa

Cantin

Decaens

et al. 2022

Chemistry A European J

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The first diastereo-and enantioselective cyclopropanation reactions of electron-deficient allenes with donor-acceptor and diacceptor diazo reagents are described. The desired enantioenriched alkylidenecyclopropanes (ACPs) were obtained in high yields with high diastereo-and enantioselectivities in the presence of Rh 2 ((S)-TCPTAD) 4 or Rh 2 ((R)-BTPCP) 4 catalysts (up to 95 % yield, > 95 : 5 d.r. and 99 : 1 e.r.). This methodology gave a direct access to ACPs bearing multiple electron-deficient substituents and allows to further expand the availability of ACPs chemistry. Interestingly, during the examination of the scope of this reaction, the asymmetric intramolecular CÀ H insertion reaction into tert-butyl group was observed as a side reaction with up to 94 : 6 e.r.

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Synthesis of pyrazolidinone fused cinnolines via the cascade reactions of 1-phenylpyrazolidinones with vinylene carbonate

Zhang

Fan

2022

Tetrahedron Letters

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Synthesis of spirocyclopropylpyrazole derivatives via the cascade reaction of alkylidenecyclopropanes with pyrazolidinones and trifluoroethanol

Abstract: A novel synthesis of spirocyclopropylpyrazole derivatives tethered with a trifluoromethyl unit through an unprecedented cascade reaction of alkylidenecyclopropanes with pyrazolidinones and trifluoroethanol (TFE) has been developed. Mechanistically, the reaction involves...

Cited by 7 publications

References 63 publications

C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds

C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds

Catalytic Asymmetric Syntheses of Alkylidenecyclopropanes from Allenoates with Donor‐Acceptor and Diacceptor Diazo Reagents

Synthesis of pyrazolidinone fused cinnolines via the cascade reactions of 1-phenylpyrazolidinones with vinylene carbonate

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