54245-36-2Relevant academic research and scientific papers
Pivotal role of intramolecular catalysis in the selective acetylation of alkyl amines
Nishida, Elvis N.,Vitto, Ramon,Peixoto, R?mulo C.R.,Nome, Faruk,Souza, Bruno S.
, (2018/04/14)
Preparation of amides by the use of esters as the "acyl donor" is less explored because they are less reactive and usually more steric demanding than conventional acid halides and anhydrides. Here, we report that 3-acetoxy-2-naphthoic acid, an aspirin analogue, can be used as a mild amine acetylating agent in ethanol at 25°C. The reaction is sensitive to steric and polar effects of the attacking amine, and the rate constants can be appropriately fitted by the Pavelich-Taft correlation. Density functional theory calculations used to study all reaction steps indicate that the o-carboxy group plays a pivotal role, guiding the attacking amine and accelerating the reaction. The reaction can be conveniently used for the acylation of a variety of primary and secondary amines.
