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One-pot synthesis of isoxazoles from enaminones: an application of Fe(II) as the catalyst for ring expansion of 2H-azirine intermediates
Authors:Yunhui Zheng  Chao Yang  Daisy Zhang-Negrerie  Yunfei Du  Kang Zhao
Affiliation:1. Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China;2. Synergetic Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China
Abstract:We report an application of FeCl2 as an inexpensive, nontoxic, and efficient catalyst in a clean ring expansion reaction of 2H-azirine derivatives, an intermediate formed through the PhI(OAc)2-mediated azirination of readily available enaminones. An alternative one-pot protocol for the synthesis of various substituted isoxazoles from their corresponding enaminones has been further established based on this reaction, and herein described.
Keywords:BHAXDAUULXCVEK-UHFFFAOYSA-N   CBPUZXDGLGAVDM-UHFFFAOYSA-N   XGUCHBNMFVITGP-UHFFFAOYSA-N   IPIVGHFCNGEUJP-UHFFFAOYSA-N   MCOYCMSBSPWRPU-UHFFFAOYSA-N   LYINQTKNIZFEDX-UHFFFAOYSA-N   GHPMYVUZFDQEHC-UHFFFAOYSA-N   CKRLFMMPXKLDSC-UHFFFAOYSA-N   XCMKEQCJJPNXRQ-DHZHZOJOSA-N   KSHUALQVZZDGDN-FMIVXFBMSA-N   XVQDEXPNNBTNJW-XYOKQWHBSA-N   GPKDPGHAGPHLIG-YRNVUSSQSA-N   RVOTWDZBHMANBS-QINSGFPZSA-N   FYWLYSOINWURRI-ZCXUNETKSA-N   VUFWZGMWCXGCDF-MRCUWXFGSA-N   NTVIDCIMRXHKMZ-SSZFMOIBSA-N
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