Chinese Journal of Organic Chemistry >
Regioselective Synthesis of Substituted Pyrazoles via[3+2]/[2+3] Cyclization of Saturated Ketone with Hydrazine/Aldehyde Hydrazone
Received date: 2019-03-23
Revised date: 2019-05-14
Online published: 2019-05-21
Supported by
Project supported by the National Natural Science Foundation of China (No. 21572047) and the Plan for Scientific Innovation Talents of Henan Province (No. 184200510012).
A highly convenient and regioselective synthesis of 1,3-disubstituted pyrazoles or 1,3,4-trisubstituted pyrazoles from Cu(Ⅱ)-catalyzed cascade reactions of saturated ketones with hydrazines or aldehyde hydrazones is presented. Mechanistically, the formation of 1,3-disubstituted pyrazoles involves the in situ generation of an enone intermediate followed by its[3+2] annulations with hydrazine. On the other hand, the formation of 1,3,4-trisubstituted pyrazoles is believed to go through a cascade process including enone formation and its subsequent[2+3] annulation with aldehyde hydrazone. Compared with literature methods, the notable features of the protocol include simple starting materials, general and broad substrate scope, high regioselectivity, good efficiency and excellent atom-economy.
Shi Xiaonan , Tian Miaomiao , Wang Muhua , Zhang Xinying , Fan Xuesen . Regioselective Synthesis of Substituted Pyrazoles via[3+2]/[2+3] Cyclization of Saturated Ketone with Hydrazine/Aldehyde Hydrazone[J]. Chinese Journal of Organic Chemistry, 2019 , 39(6) : 1630 -1641 . DOI: 10.6023/cjoc201903046
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