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An Influence of Structure of Ester on Results of Its Macrocyclization Reaction with α,ω-Diamine

Abstract Sodium methoxide was found to be an excellent catalyst in the reaction of diesters with diamines leading to macrocyclic diamides. Time of reaction was shortened to several hours (in the case of reactive esters) or to several days (in the case of less reactive esters). The template effect of Na+ ion was excluded. It was also proposed that the electron density on the carbonyl group in various esters was responsible for different results of amidation reactions. Decrease in electron density increases the reactivity of the carbonyl group. For esters 1–5, the inductive effect of the heteroatom at the α position to the carbonyl group influences reactivity mostly.