One-pot FeCl<sub>3</sub>-catalyzed sustainable synthesis of pyrimidines using ammonium iodide, aldehydes and alkyl lactate as raw materials

Fu, Meitian; Li, Jingpeng; Zhang, Zhou; Wan, Juan; Yuan, Minglong; Huang, Chao

doi:10.1039/d4gc02655a

Green Chem.

2024

DOI: 10.1039/d4gc02655a

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One-pot FeCl₃-catalyzed sustainable synthesis of pyrimidines using ammonium iodide, aldehydes and alkyl lactate as raw materials

Meitian Fu,

Jingpeng Li,

Zhou Zhang

et al.

Abstract: Iron(III)- and iodide-promoted efficient synthesis of pyrimidines from biomass-based alkyl lactates, inorganic ammonium, and aldehydes was carried out. This multicomponent reaction is efficiently proceeded through a series of condensation, dehydrogenation...

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Cited by 2 publications

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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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Ionic Liquid–Catalyzed Annulation of Biomass-Derived Alkyl Lactates: Time-Dependent Tunable Synthesis of Bioactive Dihydroquinoxalines and Quinoxalines

Liu,

Li,

Zhang

et al. 2024

ACS Sustainable Chem. Eng.

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Recyclable ionic liquid−catalyzed tandem annulation of alkyl lactates has been demonstrated, enabling divergent synthesis of dihydroquinoxalines and quinoxalines as a function of reaction time. Notably, dihydroquinoxalines could be furnished swiftly at room temperature with high yields. More significantly, the tunable synthesis is exemplified by repeatably stopping−restarting processes. Furthermore, biological studies indicate that dihydroquinoxalines with alkoxycarbonyl substitution at the C4 position are promising agrochemical candidates in terms of their antifungal activity. This method features the advantages of biomass utilization (RP > 75%), eco-benign manner (E-factor < 3), and the capacity for antileishmanial agent synthesis. Mechanistic studies established a kinetic preference for the formation of dihydroquinoxaline rather than quinoxaline through decarboxylation being thermodynamically favored. The current study reveals that reaction time could modulate the selective conversion of lactates and demonstrates the feasibility of the production of biologically valuable heterocycles from biomass.

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One-pot FeCl₃-catalyzed sustainable synthesis of pyrimidines using ammonium iodide, aldehydes and alkyl lactate as raw materials

Abstract: Iron(III)- and iodide-promoted efficient synthesis of pyrimidines from biomass-based alkyl lactates, inorganic ammonium, and aldehydes was carried out. This multicomponent reaction is efficiently proceeded through a series of condensation, dehydrogenation...

Cited by 2 publications

References 109 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

Ionic Liquid–Catalyzed Annulation of Biomass-Derived Alkyl Lactates: Time-Dependent Tunable Synthesis of Bioactive Dihydroquinoxalines and Quinoxalines

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One-pot FeCl3-catalyzed sustainable synthesis of pyrimidines using ammonium iodide, aldehydes and alkyl lactate as raw materials

Abstract: Iron(III)- and iodide-promoted efficient synthesis of pyrimidines from biomass-based alkyl lactates, inorganic ammonium, and aldehydes was carried out. This multicomponent reaction is efficiently proceeded through a series of condensation, dehydrogenation...

Cited by 2 publications

References 109 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

Ionic Liquid–Catalyzed Annulation of Biomass-Derived Alkyl Lactates: Time-Dependent Tunable Synthesis of Bioactive Dihydroquinoxalines and Quinoxalines

Contact Info

Product

Resources

About

One-pot FeCl₃-catalyzed sustainable synthesis of pyrimidines using ammonium iodide, aldehydes and alkyl lactate as raw materials

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