The synthesis of 3-carboxymethyleneazetidinones

Abstract

A series of novel azetidinones bearing the methoxycarbonylmethylene, thioethoxycarbonylmethylene, and alkylaminocarbonylmethylene side chain in their three position have been synthesized from the reaction of the potassium salt of 4,4′-bis(thioethoxy)-3-butenoic acid with a number of Schiff bases.

Development of a Process for Triazine-Promoted Amidation of Carboxylic Acids

“…We theorized that use of the trichlorotriazine promoter would permit the use of only 0.33−0.5 mol of triazine reagent per mole of carboxylic acid employed. We found several references to the use of cyanuric chloride for amidation, but the procedures were not well suited to scale-up. The triazine reagent and carboxylic acid were typically employed in a 1:1 ratio, which circumvents the advantage of employing the trichlorotriazine reagent.…”

One-step Synthesis of β-lactams Using Cyanuric Fluoride

“…Previously cyanuric chloride has been used for activation of acids in the synthesis of 2-azetidinones, although generally this method requires the cooling of the mixture below 0 °C 23,24 and the yields using cyanuric chloride above 0 °C are low. 25 However, synthesis of 2-azetidinones using cyanuric fluoride, unlike cyanuric chloride and some other acid activators, was performed at room temperature with high yield of products under simple and mild conditions.…”