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Paper | Regular issue | Vol 100, No. 8, 2020, pp.1218-1232
Published online, 3rd July, 2020
DOI: 10.3987/COM-20-14276
Efficient Synthesis of 2-Functionalized Benzoxazoles Catalyzed by Copper Iodide

Han Cao,* Xue-Jing Liu,* Fu-sheng Bie, Peng Yan, Jie Ma, Yi-jun Shi, and Ying Han

*Engineering and Technology Research Institute of Lunan Coal Chemical,, Zaozhuang University, 1 Beian Road, China


We reported an efficient synthesis of 2-functionalized benzoxazoles in mild condition and excellent yields. The synthetic process includes two steps. The step one contains a reaction of pendent halide formamidine derivatives and 2- aryloxyacetyl chloride generating highly selective (Z)-N-(2-halophenyl)-3-(dime- thyllamino)-2-aryloxyacrylamides, and the step two undergoes copper iodide catalyzed intramolecular C-O bond formation to yield title compounds. This strategy is not only providing newly discovered key intermediates 6a-l which contain multiple functional groups on 2-position (as building blocks), but also expanded the scope of methodologies for making diverse benzoxazoles with multiple functional groups.