Abstract
A novel and efficient method for the synthesis of 8-(polyfluoroalkoxy)-1-azaspiro[4.5]deca-3,6,9-trien-2-ones
has been demonstrated via the electrophilic ipso -halocyclization
of N -arylpropynamides with polyfluoroalkyl
alcohols. In the presence of N -halosuccinimides
(NXS), a variety of N -arylpropynamides
underwent an electrophilic ipso -halocyclization
reaction with polyfluoroalkyl alcohols to afford the corresponding
8-(polyfluoroalkoxy)spiro[4.5]trienes in good
yields. Note that molecular sieves can improve the yield of the
reaction.
Key words
electrophilic ipso -halocyclization -
N -arylpropynamide -
N -halosuccinimide - spiro[4.5]decane - polyfluoroalkoxy substitution
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8 The structures and the cis /trans configuration
of the products are determined on the basis of the chemical shift
of hydrogen at the 8-position of the spirocyclic motif according
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9 A set of other reagents, including
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electrophilic ortho -cyclization product 4aa was obtained in 90% yield
in the presence of TfOH.
