Premium
Synthesis of thiazole‐containing benzo‐crown ethers
Author(s) -
Kim HongSeok,
Koh Young Kook,
Choi JunHyeak
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350134
Subject(s) - chemistry , thiazole , crown (dentistry) , 15 crown 5 , stereochemistry , medicinal chemistry , organic chemistry , crown ether , dentistry , medicine , ion
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.