A series of benzo-crown ethers containing the thiazole subcyclic moity
have been synthesized. Reaction of 1,2-bis(thioamidomethyloxy)benzene
2 with ethyl bromopyruvate in ethanol provided 1,2-bis(thiazolyl)benz
ene 4 (80%) along with thiazole 5 (14%). Reduction of 4 with lithium a
luminum hydride followed by mesylation-bromination gave 7. Similar tre
atment of 5 with Lithium aluminum hydride followed by bromination resu
lted in 12. Benzocrown ethers 8, 9, 10, and 13 were prepared from the
reactions of 4-bromomethylthiazole derivatives 7 and 12 with catechol
and resorcinol derivatives in the presence of potassium hydride.