One-step Synthesis of β-lactams Using Cyanuric Fluoride

Abstract

Cyanuric fluoride works as an efficient acid activator reagent for the direct [2+2] ketene-imine cycloaddition of substituted acetic acids and imines in a one-pot synthesis under mild conditions. The yields are good to excellent and the reaction conditions are mild, simple and efficient.

Tosylimidazole-mediated one-pot synthesis of 2-azetidinones

“…11,12 However, owing to their instability and the lack of availability of acyl chlorides and sometimes the low yield of products, direct generation of ketenes from carboxylic acids using acid activators has been considered. [12][13][14][15][16][17][18][19][20] Here, we report the use of tosylimidazole as a coupling reagent for the one-pot synthesis of 2-azetidinones from carboxylic acids and imines.…”

Facile Synthesis of β-Lactam Derivatives by the Staudinger Reaction Using 3,6-Dichlorotetrazine

“…6,7 Also, the reaction of acyl chlorides with triethyamine has been used for the generation of the ketenes. 8 Acyl chlorides are unstable in the presence of moisture, some of them are not commercially available and their synthesis and purification can be difficult. Activation of a carboxylic acid with acid activator reagents followed by treatment with a base is another method for ketene generation without using acid halides.…”