Synthesis of N-methyl secondary amides via diboronic acid anhydride-catalyzed dehydrative condensation of carboxylic acids with aqueous methylamine DOI

H. IWASAWA,

Naoya Takahashi, Naoyuki Shimada

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер 23(10), С. 2400 - 2410

Опубликована: Янв. 1, 2025

In this study, we present the first catalytic methodology for synthesizing N-methyl secondary amides via dehydrative condensation of hydroxycarboxylic acids with readily available and safe aqueous methylamine, employing diboronic acid anhydride (DBAA) as catalyst. DBAA catalysis can also be applied to direct amidations using ethylamine or dimethylamine. Moreover, demonstrate applicability system concise synthesis eight biologically active compounds containing β-amino alcohol motifs, including halostachine, synephrine, longimammine, phenylephrine, metanephrine, normacromerine, etilefrine, macromerine.

Язык: Английский

Synthesis of N-methyl secondary amides via diboronic acid anhydride-catalyzed dehydrative condensation of carboxylic acids with aqueous methylamine DOI

H. IWASAWA,

Naoya Takahashi, Naoyuki Shimada

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер 23(10), С. 2400 - 2410

Опубликована: Янв. 1, 2025

In this study, we present the first catalytic methodology for synthesizing N-methyl secondary amides via dehydrative condensation of hydroxycarboxylic acids with readily available and safe aqueous methylamine, employing diboronic acid anhydride (DBAA) as catalyst. DBAA catalysis can also be applied to direct amidations using ethylamine or dimethylamine. Moreover, demonstrate applicability system concise synthesis eight biologically active compounds containing β-amino alcohol motifs, including halostachine, synephrine, longimammine, phenylephrine, metanephrine, normacromerine, etilefrine, macromerine.

Язык: Английский

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