Base-Mediated Synthesis of Anhydrides from Activated Amides

Abstract

Symmetrical anhydrides were synthesized from activated amides such as N-benzoylsaccharins and N-Boc-protected benzamides. The activated amides reacted with H 2 O in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 25 °C to produce the corresponding symmetrical anhydrides in high yields through C−N bond cleavage. In addition, N-benzoylsaccharins reacted with benzoic acid derivatives to generate unsymmetrical anhydrides in high yields.

Facile Cleavage of Activated Ketones: An Access to Thioethers via In Situ Generation of Anhydrides by Pummerer-Type Rearrangement

“…Moreover, Pd-catalyzed carbonylation and cross-dehydrogenative coupling of aldehydes with carboxylic acid have also been reported . Recently, anhydrides were synthesized from activated amides by the Szostak and Lee research group (Scheme a). However, ketones are not well explored as acylating reagents because of their low reactivity.…”

Reductive cross-coupling of N-acyl pyrazole and nitroarene using tetrahydroxydiboron: synthesis of secondary amides

“…Recently, we have developed several amide transformations for the synthesis of other amides, ketones, esters, acyl azides, and ketonitriles. 9 During the studies of amide transformations, we paid attention to acyl pyrazoles as acylating reagents for the synthesis of amides. Acyl pyrazoles are important building blocks in organic synthesis as intermediates for the preparation of a variety of other organic molecules.…”