Journal of Heterocyclic Chemistry p. 177 - 181 (1998)
Update date:2022-08-03
Topics:
Kim, Hong-Seok
Koh, Young Kook
Choi, Jun-Hyeak
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)benzene 4 (80%) along with thiazole 5 (14%). Reduction of 4 with lithium aluminum hydride followed by mesylation-bromination gave 7. Similar treatment of 5 with lithium aluminum hydride followed by bromination resulted in 12. Benzo-crown 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.
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