Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Synthesis of 4-Acylpyrazoles from Saturated Ketones and Hydrazones Featured with Multiple C(sp3)–H Bond Functionalization and C–C Bond Cleavage and Reorganization

Synthesis of 4-Acylpyrazoles from Saturated Ketones and Hydrazones Featured with Multiple C(sp3)–H Bond Functionalization and C–C Bond Cleavage and Reorganization
Xiaonan Shi, Miaomiao Tian, Xuesen Fan, Xinying Zhang
In this paper, an efficient and convenient one-pot synthesis of diversely substituted 4-acylpyrazole derivatives via copper-catalyzed one-pot cascade reactions of saturated ketones with hydrazones is reported. Mechanistically, the formation of the title compounds involves the in situ formation of an enone intermediate through the dehydrogenation of a saturated ketone and the [2 + 3] cyclization of the enone with hydrazone followed by an aromatization-driven C–C bond cleavage and reorganization. To our knowledge, this is the first example in which the biologically and pharmaceutically important yet otherwise difficult-to-obtain 4-acylpyrazole derivatives are directly prepared from saturated ketones and hydrazones featured with multiple aliphatic C–H bond functionalization and C–C bond cleavage and reorganization. Compared with literature methods, this novel process has advantages such as simple and economical starting materials, a sustainable oxidant, excellent regioselectivity, and good efficiency.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01013

DOI: 10.1021/acs.joc.7b01013

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