Anionic Triflyldiazomethane: Generation and Its Application for Synthesis of Pyrazole-3-triflones via [3 + 2] Cycloaddition Reaction
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- Pulakesh Das
- Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku Nagoya 466-8555, Japan
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- Satoshi Gondo
- Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku Nagoya 466-8555, Japan
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- Etsuko Tokunaga
- Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku Nagoya 466-8555, Japan
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- Yuji Sumii
- Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku Nagoya 466-8555, Japan
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- Norio Shibata
- Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku Nagoya 466-8555, Japan
書誌事項
- 公開日
- 2018-01-10
- 資源種別
- journal article
- DOI
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- 10.1021/acs.orglett.7b03664
- 公開者
- American Chemical Society (ACS)
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説明
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.
収録刊行物
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- Organic Letters
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Organic Letters 20 (3), 558-561, 2018-01-10
American Chemical Society (ACS)
