New crown compounds containing a 1,3,4-thiadiazole moiety: Synthesis and crystal structure

The syntheses of new macrocyclic compounds are described. The 2,5-bis(hydroxyphenyl)-1,3,4-thiadiazole reacts with allyl bromide to give the corresponding allyloxy derivative. The allyl is used to functionalize the ortho position by means of a Claisen rearrangement under microwave irradiation. New 2,5-dihydroxyphenyl-1,3,4-thiadiazoles are obtained, which are converted into macrocyclic polyethers. The structures of the new macrocyclic compounds were confirmed by H-1, C-13 NMR, and mass spectroscopy. The crystal structure of 2,5-bis(2-allyloxyphenyl)-1,3,4-thiadiazole has been determined.