Synthesis of 2-Iodobenzamide Derivatives

Abstract

Iodoamide derivatives are one of the most privileged structure motifs frequently found in natural products, pharmaceuticals, functional materials, and medicines. Synthesis and biological evaluation of Iodoamide derivatives have been a topic of special interest to organic and medicinal chemist. Here a convenient method for the synthesis of 4,4- disubstituted and 2,4- disubstituted amide derivatives through palladium catalyzed crosscoupling reaction and without palladium catalyzed cross-coupling reaction is reported. In this purpose, 2,6- diiodo – 4 –substituted ,2-iodo-4-substituted, and 2-iodo -6- substituted anilines 4, 5, 6 were synthesized by the iodination of their parent 4-sustituted and 2 - substituted anilines using KI, KIO3 in methanol. The cross-coupling reaction of 2,6- diiodo – 4 –substituted anilines and 2-iodo-4-substituted anilines 4, 5 with acid chloride were carried out in the presence of (Ph3P)2PdCl2 in MeCN at room temperature for 24-48 hrs. under nitrogen atmosphere to yield N-(2,6-diiodo-4-substituted phenyl)-p-substituted benzamide and N-(2-iodo-4-substituted phenyl)-p-substituted benzamide 7, 8. Again the reaction study on 2,6- diiodo–4–substituted, 2-iodo-4- substituted and 2-iodo-6- substituted anilines e.g.on 4, 5, 6 with acid chlorides were carried out in benzene at room temperature for 24-48 hrs under N2 atmosphere to yield N-(2,6-diiodo-4-substituted phenyl)- p-substituted benzamide, N-(2-iodo-4-substituted phenyl)- p-substituted benzamide and -(2-iodo-6-substituted phenyl)- p-substituted benzamide 7, 8, 9 & 10.-----------------------------------