Novel synthesis of cyclic tertiary enamides from 2-acetylbenzoic acid

Cyclic tertiary-enamides act as nucleophiles in reactions. This makes tertiary-enamides important in many organic syntheses, especially for compounds with any nitrogen containing functional groups. There is evidence of previous methods to synthesize cyclic tertiary-enamides; however, it is ideal to do so in a manner that is quick and cost-effective. The purpose of this research is to develop a procedure to synthesize cyclic-tertiary enamides that is simple and efficient. The focus of this research is a method to synthesize cyclic tertiary-enamides from 2-acetylbenzoic acid and aniline in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. By varying substituents on aniline, analogues of 3-methylene-2-arylisoindolin-1-ones, a type of cyclic tertiary-enamide, can be formed as a result. Eight different analogues were synthesized by this method. Each product was characterized using 1H and 13C{1H} NMR spectroscopy and HRMS data.