Synthesis of some 24-membered tetralactam derivatives by an unexpectedly simple route, and some macrocyclic polyether dilactams

Article abstract of DOI:10.1016/S0040-4020(99)00892-3

An unexpected reaction of 1,5-bis(arylamino)-3-oxapentanes 41 21 and 22 with diglycolyl dichloride gave 24-membered macrocyclic tetralactams 18, 23 and 24 respectively, in a reaction involving two molecules of each reactant (2:2 process). This was in contrast to closely related reactions of α,ω- bis(arylamino)alkylethers 5 and 6 with diglycolyl, triglycolyl and tetraglycolyl dichlorides which yielded the macrocycles 9-14 by reaction of one molecule of each reactant (1:1 process). The phenyl nuclei in 14 and 18 were formulated to give 34, 35 and 36. The aldehydes, 35 and 36 were condensed with a quinoxaline fluorophore to yield the diene 37 and the tetraene 38 respectively.