Synthesis of novel lariat azathia crown macrocycles containing two triazole rings and bis crown macrocycles containing four triazole rings

The 13-hydroxy macrocycles were prepared in 40–50% yields by the condensation of 1,ω-bis(4-amino-1,2,4-triazol-3-ylsulfany)alkanes with 1,3-bis(2-formyphenoxy)-2-propanol (). Acylation of with 2-chloroacetylchloride gave the corresponding esters . Amination of with different amines in acetone furnished exclusively the target lariat macrocycles and in 60–70% yields. Reaction of 2 equiv. of the macrocycles with 1 equiv. of piperazine afforded the novel bis macrocyles in 50–60% yields. Reduction of with NaBH4 afforded the corresponding 13-hydroxyazathia crown ethers in 65–70% yields.