Synthesis of 5-Amino-3(2<i>H</i>)-furanones via <i>S</i>-Methylation/Intramolecular Cyclization of Î³-Sulfanylamides.

Inagaki, Sho; Omichi, Riko; Yamazaki, Kei; Shibuta, Yuzuka; Kawano, Tomikazu

Synthesis of 5-Amino-3(2H)-furanones via S-Methylation/Intramolecular Cyclization of Î³-Sulfanylamides.

Inagaki, Sho; Omichi, Riko; Yamazaki, Kei; Shibuta, Yuzuka; Kawano, Tomikazu.

Afiliación

Inagaki S; Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan.
Omichi R; Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan.
Yamazaki K; Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan.
Shibuta Y; Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan.
Kawano T; Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan.

J Org Chem ; 89(10): 6770-6782, 2024 May 17.

Article en En | MEDLINE | ID: mdl-38691345

ABSTRACT

ABSTRACT

The S-methylation/intramolecular cyclization of Î³-sulfanylamide is depicted. Different methylating reagents were successfully employed for S-methylation, depending on the substituent pattern of the amide in the starting Î³-sulfanylamides; trimethyloxonium tetrafluoroborate was used for N-aryl substituted Î³-sulfanylamides, and the combination of methyl iodide and silver(I) tetrafluoroborate was used for N-alkyl substituted Î³-sulfanylamides. 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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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos

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