Synthesis of macroheterocycles, analogs of dibenzo-crown compounds. 1. 15-membered oxathiadiamines

Abstract

Macrocyclic diamides have been synthesized by the condensation of 1,4-bis(2-aminophenyl)-1,4-dioxa(dithia)butanes with the diacid chlorides of glutaric, diglycolic, and thiodiglycolic acids under conditions of high dilution. Subsequent reduction with diborane led to the corresponding macrocyclic diamine containing atoms of oxygen and (or) sulfur. Structural assignments were made using data of mass spectrometry and IR, PMR, and 13C NMR spectra.