Synthesis of Bis{(S‐methyl)azolespoly(ethylene oxide)} from 3,6‐dioxa‐1,8‐octanedithiol

Bis(1,3,4-oxadiazoles) 4, 5 and bis(1,2,4-triazoles) 6a, 6b have been prepared from 3,6-dioxa-1,8-octanedithiol 1 through a multistep reaction sequence. Compound 4 reacted with the appropriate alkyl halide in the presence of potassium carbonate in refluxing acetone to give the corresponding bis(S-alkylated-1,3,4-oxadiazoles) 7a, 7b. The title compound 8 was prepared by condensing 4 with benzoyl bromide in the presence of triethylamine. Further, 6,9-dioxa-3,12-dithiotetradecanedihydrazide 3 was converted to bis{N′-(phenylaminocarbonyl) hydrazides} and bis{N′-(phenylaminocarbonothioyl)hydrazides} 9a, 9b using phenylisocyanate and phenylthioisocyanate, respectively, which underwent cyclization in alkaline medium to produce 6,9-dioxa-3,12-dithiotetradecane bis(4-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one) and their 3-thio analogs 10a, 10b. The new compounds 4, 5, 6, 7, 8, 9, 10 were characterized by their IR, 1H-NMR, 13C-NMR, MS, and elemental analyses.