110920-05-3Relevant academic research and scientific papers
Synthesis of 4-fluoromethylsydnones and their participation in alkyne cycloaddition reactions
Foster, Robert S.,Adams, Harry,Jakobi, Harald,Harrity, Joseph P. A.
, p. 4049 - 4064 (2013/06/05)
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.
A general and regioselective synthesis of 5-trifluoromethyl-pyrazoles
Foster, Robert S.,Harrity, Joseph P. A.,Jakobi, Harald
supporting information, p. 4858 - 4861,4 (2012/12/12)
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.
REACTIONS OF HIGHLY ELECTROPHILIC POLYFLUOROCARBONYL COMPOUNDS WITH PRIMARY ARYLAMINES
Chkanikov, N. D.,Sviridov, V. D.,Zelenin, A. E.,Galakhov, M. V.,Kolomiets, A. F.,Fokin, A. V.
, p. 323 - 328 (2007/10/02)
C-Hydroxyalkylation of primary arylamines by highly electrophilic polyfluorocarbonyl compounds results from the direct reaction of the initial reagents and is competitively inhibited by equilibrium N-hydroxyalkylation.The presence of steric hindrances to
FLUORINE-CONTAINING AMINO ACIDS. III. α-TRIFLUOROMETHYL AMINO ACIDS
Soloshonok, V. A.,Gerus, I. I.,Yagupol'skii, Yu. L.,Kukhar', V. P.
, p. 2034 - 2038 (2007/10/02)
A convenient method was developed for the synthesis of α-trifluoromethyl amino acids by the alkylation of the previously unknown imines of methyl 3,3,3-trifluoropyruvate with organometallic reagents.The differences in the reactivity of the imines in relation to the substituent at the nitrogen atom were demonstrated.
