3 years ago

Anionic Triflyldiazomethane: Generation and Its Application for Synthesis of Pyrazole-3-triflones via [3 + 2] Cycloaddition Reaction

Anionic Triflyldiazomethane: Generation and Its Application
for Synthesis of Pyrazole-3-triflones via [3 + 2] Cycloaddition Reaction
Norio Shibata, Pulakesh Das, Etsuko Tokunaga, Satoshi Gondo, Yuji Sumii
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03664

DOI: 10.1021/acs.orglett.7b03664

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