Synthesis of Fluoro 3(2H)-Furanones via a TFA-Catalyzed Dehydrofluorinative Cyclization of 2,2-Difluoro-3-hydroxy-1,4-diketones

Li, Rongyao; Zhang, Jing; Sun, Manman; Xu, Jinjing; Huang, Guo-Bo; Yan, Jianbo; Yang, Jianguo; Wang, Zhiming; Ma, Chao

doi:10.1021/acs.orglett.3c02765

Org. Lett.

2023

DOI: 10.1021/acs.orglett.3c02765

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Synthesis of Fluoro 3(2H)-Furanones via a TFA-Catalyzed Dehydrofluorinative Cyclization of 2,2-Difluoro-3-hydroxy-1,4-diketones

Rongyao Li,

Jing Zhang,

Manman Sun

et al.

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2024

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Synthesis of 5-Amino-3(2H)-furanones via S-Methylation/Intramolecular Cyclization of γ-Sulfanylamides

Inagaki,

Omichi,

Yamazaki

et al. 2024

J. Org. Chem.

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The S-methylation/intramolecular cyclization of γsulfanylamide is depicted. Different methylating reagents were successfully employed for S-methylation, depending on the substituent pattern of the amide in the starting γ-sulfanylamides; trimethyloxonium tetrafluoroborate was used for N-aryl substituted γ-sulfanylamides, and the combination of methyl iodide and silver(I) tetrafluoroborate was used for N-alkyl substituted γsulfanylamides. When the resulting sulfonium salt was treated with DBU, it smoothly underwent intramolecular cyclization to produce a series of N-aryl, N-alkyl, N,N-dialkyl or N-alkyl-N-aryl substituted 5-amino-3(2H)-furanones in 55%−quantitative yields.

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Synthesis of 5-Amino-3(2H)-furanones via S-Methylation/Intramolecular Cyclization of γ-Sulfanylamides

Inagaki,

Omichi,

Yamazaki

et al. 2024

J. Org. Chem.

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show abstract

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Synthesis of Fluoro 3(2H)-Furanones via a TFA-Catalyzed Dehydrofluorinative Cyclization of 2,2-Difluoro-3-hydroxy-1,4-diketones

Cited by 1 publication

References 38 publications

Synthesis of 5-Amino-3(2H)-furanones via S-Methylation/Intramolecular Cyclization of γ-Sulfanylamides

Synthesis of 5-Amino-3(2H)-furanones via S-Methylation/Intramolecular Cyclization of γ-Sulfanylamides

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