Synthesis of mixed-donor azaoxathia macrocyclic tetraamides, acyclic polyether di/and tetraamides and their c-pivot lariat derivatives

The macrocyclic tetraamides 11a-e and 15-hydroxy macrocyclic tetraamides 23a-c were prepared in good yields by the nucleophilic reaction of the potassium salts of the bis-phenoles 10a-c with the appropriate dihalo compounds 5a-d and 15. Moreover, the acyclic diamides 7, 9, 17-21 and bis-acyclic tetraamide 22 were obtained in high yields by the reaction of the appropriate dichloro compounds with different phenoxides and secondary amines. Acylation of 23a-c with different acid chlorides gave the corresponding esters 24a-c. Compounds 24a-c reacted with different secondary amines to afford the corresponding novel lariat macrocycles 25a-d in high yields.