Poly(methyl methacrylate)-supported hydroxamic dithiocarbonic anhydrides: preparation and use as acyl transfer reagents

Abstract

The use of poly(methyl methacrylate) (PMMA)-supported hydroxamic dithiocarbonic anhydrides in the synthesis of amides is illustrated. The reagent was found to selectively acylate amines and amino acids to give the corresponding amides. The efficiency of the acyl transfer reaction was found to be affected by the nature of the crosslinking agent, the nature of the solvent, the temperature, the reaction period, and the effective concentration of the reagent function. The percentage yield of amides obtained using N,N′-methylene-bis-acrylamide (N,N′-MBA)-crosslinked hydroxamic dithiocarbonic anhydride resins was found to be higher than that of ethylene glycol dimethacrylate (EGDMA)- and divinylbenzene (DVB)-crosslinked ones. It was also observed that the extent of acylation was higher in polar solvents such as acetonitrile. The acyl transfer reaction was favored by high temperature and with a high resin to amine ratio.

Keywords:

• Polymeric reagents
• acyl transfer reagents
• acylation of amines
• PMMA support
• selective acylation