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通过可见光催化,α-溴代酮与腙的自由基加成反应制备 1,3,5-三取代吡唑。

Radical Addition of Hydrazones by α-Bromo Ketones To Prepare 1,3,5-Trisubstituted Pyrazoles via Visible Light Catalysis.

机构信息

Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry and University of Chinese Academy of Sciences, Chinese Academy of Sciences , Beijing 100190, P. R. China.

出版信息

J Org Chem. 2016 Aug 19;81(16):7127-33. doi: 10.1021/acs.joc.6b00992. Epub 2016 Jul 14.

Abstract

A novel efficient tandem reaction of hydrazones and α-bromo ketones is reported for the preparation of 1,3,5-trisubstituted pyrazoles by visible light catalysis. In this system, the monosubstituted hydrazones show wonderful reaction activity with alkyl radicals, generated from α-bromo ketones. A radical addition followed by intramolecular cyclization affords the important pyrazole skeleton in good to excellent yields. This efficient strategy under mild conditions with wide group tolerance provides a potential approach to the 1,3,5-trisubstituted pyrazoles.

摘要

本文报道了一种通过可见光催化合成 1,3,5-三取代吡唑的新型高效串联反应,该反应涉及腙和α-溴代酮。在该体系中,单取代腙与α-溴代酮生成的烷基自由基反应活性很高。自由基加成后进行分子内环化,以良好到优秀的收率得到重要的吡唑骨架。该方法在温和条件下、基团容忍度较宽,具有很高的效率,为 1,3,5-三取代吡唑的合成提供了一种潜在方法。

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