Synthesis of 4-fluoromethylsydnones and their participation in alkyne cycloaddition reactions
We report the synthesis and some structural studies of 4-trifluoromethyl, 4-difluoromethyl-, and 4-monofluoromethylsydnones. All but the latter compounds are stable and represent effective precursors to a range of pyrazoles after cycloaddition reactions with alkynes. The cycloadditions are generally highly regioselective and provide 5-fluoromethylpyrazole products, although we have observed that Bn-substituted sydnones can provide an unexpected alkyne insertion mode that generates the 3-fluoromethyl isomer.
Foster, Robert S.,Adams, Harry,Jakobi, Harald,Harrity, Joseph P. A.
p. 4049 - 4064
(2013/06/05)
A general and regioselective synthesis of 5-trifluoromethyl-pyrazoles
Two synthetic approaches to 4-trifluoromethylsydnones, a novel class of these mesoionic reagents, are reported. These compounds undergo regioselective alkyne cycloaddition reactions, thereby providing a general approach to 5-trifluoromethylpyrazoles. This method has been employed in a short formal synthesis of the herbicide fluazolate.
Foster, Robert S.,Harrity, Joseph P. A.,Jakobi, Harald
p. 4858 - 4861,4
(2012/12/12)
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