Microwave-assisted One-pot Conversion of 1-(2-Hydroxyphenyl)ethanone Oximes to Benzo[d]isoxazoles Catalyzed by Sodium 2-Chloro-2,2-difluoroacetate
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O621.3;O626.2

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    Abstract:

    One-pot conversion of 1-(2-hydroxyphenyl)ethanone oximes to benzo[d]isoxazoles was achieved under microwave-assisted condition and catalyzed with sodium 2-chloro-2,2-difluoroacetate (SCDA). The effects of solvent, the amount of iodine, microwave power and reaction temperature on the reaction were considered. The optimized reaction conditions are: n(oximes):n(SCDA): n(K2CO3) = 1:1.5:1.5, in N,N-dimethylacetamide (1 mol/L for oximes), microwave power 300 W, reaction temperature 85 ℃, reaction time 35 min. Eight benzo[d]isoxazoles with different substituent groups were synthesized in 64%~93% yields under the optimized reaction conditions. The structures of all products were confirmed by the corresponding nuclear magnetic resonance spectrum (1HNMR) and mass spectrum (MS).

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History
  • Received:June 15,2016
  • Revised:November 10,2016
  • Adopted:December 01,2016
  • Online: February 09,2017
  • Published:
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