Synthesis of novel macrocyclic di‐ and tetralactams and their corresponding C‐pivot lariat derivatives

Abstract

A synthesis of novel C‐pivot lariat macrocycles incorporated amide linkages is described. The dipotassium salt of N,N′‐(2‐hydroxypropane‐1,3‐diyl)bis(2‐hydroxybenzamide) is first reacted with a variety of bis(chloro) compounds, and then the hydroxyl groups of these macrocycles are acylated with chloroacetyl chloride to give the corresponding (chloroacetoxy) derivatives. The desired products were produced in good yields through subsequent amination of the latter compounds with morpholine.