An influence of structure of ester on results of its macrocyclization reaction with alpha,omega-diamine

Sodium methoxide was found to be an excellent catalyst in the reaction of d iesters with diamines leading to macrocyclic diamides. Time of reaction was shortened to several hours tin the case of reactive esters) or to several days tin the case of less reactive esters). The template effect of Na+ ion was excluded. It was also proposed that the electron density on the carbony l group in Various esters was responsible for different results of amidatio n reactions. Decrease in electron density increases the reactivity of the c arbonyl group. For esters 1-5, the inductive effect of the heteroatom at th e alpha position to the carbonyl group influences reactivity mostly.