N-(2-aminoarylacyl)benzotriazole mediated anthranilic acid esters, thioesters, and amides synthesis and their characterization

Anthranilic acid which appears as an intermediate in the major biochemical pathways of bacteria, plants and animals is also the starting material for many compounds widely distributed in nature. Among these are alkaloids, plant signalling compounds like DIMBOA and indole-3-acetic acid. Besides this, anthranilic acid and its ester, thioester and amide derivatives are widely used in synthetic organic chemistry for the synthesis of various heterocycles. Due to its wide presence in nature and the functionality of its derivatives in synthetic processes, there is a need to develop more useful new methods and reagents which can be used in the synthesis of anthranilic acid derivatives. N-Acylbenzotriazoles provide more moderate reaction conditions in the synthesis of esters, thioesters and amides alternative to the compounds which have been used as acylating agents for many years. Therefore, in this work, novel N-(2-aminoarylacyl)benzotriazoles were first synthesized from the reaction between anthranilic acid, benzotriazole and DCC using benzotriazole methodology. Then, anthranilic acid esters, thioesters and amides were prepared in high yields with a new method different from literature by treating N-(2-aminoarylacyl)benzotriazoles with various alcohols, thioalcohols and amides. The structures of all compounds were determined by various spectroscopic methods.Keywords: Anthranilic acid, Benzotriazole, N-Acylbenzotriazole, Ester, Thioester, Amide.