Abstract
The condensation of o-aminophenol with ethyl hippurate has given 2-benzoylaminomethylbenzoxazole (I) and N-hippuroyl-o-aminophenol (II). The cyclization of both I and II in the presence of phosphorus oxychloride in benzene or toluene leads to the formation of 1-phenylimidazo[5, 1-b]benzoxazole (III). Compound III has been brominated in position 3 and has been subjected to the Mannich and Vilsmeier reactions. A number of derivatives of III containing various substituents in position 3 has been obtained.
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References
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Sycheva, T.P., Pankina, Z.A. & Shchukina, M.N. Synthesis and some reactions of 1-phenylimidazo'[5,1-b] benzoxazole. Chem Heterocycl Compd 6, 406–409 (1970). https://doi.org/10.1007/BF00478377
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DOI: https://doi.org/10.1007/BF00478377