<b>Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under <scp>Solvent‐Free</scp> Conditions</b>

Zuo, Wanqing; Zhu, Zhizhen; Cheng, Yu; Zuo, Lingling; Geng, Xiao; Li, Zhifang; Wang, Lei

doi:10.1002/cjoc.202300725

Chin. J. Chem.

2024

DOI: 10.1002/cjoc.202300725

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Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under Solvent‐Free Conditions

Wanqing Zuo,

Zhizhen Zhu,

Yu Cheng

et al.

Abstract: Comprehensive SummaryThe development of switchable solvent‐free multicomponent reactions to build high‐value‐added products is an important demand for organic synthesis. Herein, we detailed the successful implementation of a switchable strategy for the construction of diverse 4‐fluoroalkyl‐1,4‐dihydropyrimidines and 4‐fluoroalkyl‐pyrimidines via a solvent/additive‐free [3 + 2 + 1] annulation, starting from readily available enamines, trifluoroacetaldehyde hydrate or 1‐ethoxy‐2,2‐difluoroethanol and amidines hy… Show more

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Combining (CH₂O)_n and (NH₄)₂CO₃ as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines

Han,

Ren,

Tang

et al. 2024

Org. Lett.

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Multicomponent reactions hold the potential to maximize the synthetic efficiency in the preparation of diverse and complex molecular scaffolds. An unprecedented formal [3+1+1+1] annulation approach for the one-step synthesis of fluoroalkylated 2-H-pyrimidines commencing from perfluoroalkyl alkenes, paraformaldehyde, and ammonium carbonate is described. By harnessing readily accessible (CH2O) n and cheap (NH4)2CO3 as a formamidine surrogate, this method effectively replaces traditionally preformed amidines with a pyrimidine assembly. The multicomponent reaction proceeds in a step-economical, operationally simple, metal-free, and additive-free manner, featuring a broad substrate scope, excellent functional group compatibility, and scalability. The potential for the synthetic elaboration of the obtained 2-H-pyrimidine is further demonstrated in the alkylation and vinylation of its C2 position.

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Combining (CH₂O)_n and (NH₄)₂CO₃ as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines

Han,

Ren,

Tang

et al. 2024

Org. Lett.

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Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4H-pyrans

Wu,

Chen,

Yang

et al. 2024

Org. Lett.

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A three-component annulation reaction and trifluoromethylation for the construction of 3-(trifluoromethyl)-4H-pyrans using β-CF 3 -1,3-enynes, BrCF 2 CO 2 Et, and sulfoxonium ylides as readily available substrates has been developed. This metal-free process involves two C−F bond cleavages of β-CF 3 -1,3-enynes and a CF 3 group generated in situ from BrCF 2 CO 2 Et. This method is applicable to the late-stage modification of pharmaceutically active molecules.

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Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

Liu,

Tian,

et al. 2024

Org. Biomol. Chem.

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Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under Solvent‐Free Conditions

Cited by 3 publications

References 38 publications

Combining (CH₂O)_n and (NH₄)₂CO₃ as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines

Combining (CH₂O)_n and (NH₄)₂CO₃ as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines

Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4H-pyrans

Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

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Product

Resources

About

Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under Solvent‐Free Conditions

Cited by 3 publications

References 38 publications

Combining (CH2O)n and (NH4)2CO3 as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines

Combining (CH2O)n and (NH4)2CO3 as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines

Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4H-pyrans

Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

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Product

Resources

About

Combining (CH₂O)_n and (NH₄)₂CO₃ as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines

Combining (CH₂O)_n and (NH₄)₂CO₃ as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines