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Short Paper | Regular issue | Vol 89, No. 5, 2014, pp.1221-1227
Published online, 2nd April, 2014
DOI: 10.3987/COM-14-12965
One-Pot Three-Component Synthesis of 3,5-Disubstituted Isoxazoles by a Coupling–Cyclocondensation Sequence

Hai-Ling Liu,* Zhu-Feng Geng, Si-Yu Zhang, and Jie Han

*Analytical & Testing Center, Beijing Normal University, No. 19, XinJieKouWai St., HaiDian District 100875, China


A convenient one-pot procedure for the synthesis of 3,5-disubstituted isoxazoles from acid chloride, terminal alkyne, and hydroxylamine hydrochloride catalyzed by Pd(PPh3)2Cl2/CuI has been developed. The coupling of acid chlorides to terminal alkynes afforded α,β-unsaturated ynones that underwent in situ cyclocondensation with hydroxylamines to afford the desired isoxazoles in 44–76% isolated yields.