Anionic Triflyldiazomethane: Generation and Its Application for Synthesis of Pyrazole-3-triflones via [3 + 2]
Pulakesh Das1, Satoshi Gondo1, Etsuko Tokunaga1
1Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology , Gokiso-cho, Showa-ku Nagoya 466-8555, Japan.
Abstract:
The synthesis of pyrazole triflones containing a triflyl group at the 3-position is disclosed. Treatment of 2-diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one with nitroalkenes under basic conditions gave pharmaceutically attractive pyrazole 3-triflones in good to high yields. The generation of anionic triflyldiazomethane species followed by the [3 + 2] cycloaddition reaction with nitroalkenes is proposed for this transformation. 3-(Difluoromethanesulfonyl)pyrazoles were also synthesized by using a previously unknown anionic (difluoromethanesulfonyl)diazomethane species under a similar strategy.
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