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Synthesis of thiazole-containing benzo-crown ethers

✍ Scribed by Hong-Seok Kim; Young Kook Koh; Jun-Hyeak Choi

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
438 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

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 mesylationbromination 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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