Chinese Journal of Organic Chemistry >
Palladium-Catalyzed Cascade Cyclization/Bromination of 2-Alkynone O-Methyl Oximes in Ionic Liquid
Received date: 2018-12-04
Revised date: 2019-01-01
Online published: 2019-01-18
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21502055, 21642005), the Fundamental Research Funds for the Central Universities (No. 2018ZD16) and the National Training Program of Innovation and Entrepreneurship for Undergraduates (No. 201810561075).
An efficient palladium-catalyzed protocol for the synthesis of 4-bromoisoxazoles derivatives in moderate to good yields from readily available O-methyl oximes in basic ionic liquid has been developed. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. This cascade cyclization/bromination process provides a novel route for directly accessing 4-bromoisoxazole in good to excellent yields and good functional group tolerance with high atom efficiency. Notably, the current methodology could also be conveniently applied to the synthesis of isoxazoles naturally occurring biologically active frameworks.
Li Jianxiao , Lin Shao , Huang Ruikang , Li Can , Yang Shaorong . Palladium-Catalyzed Cascade Cyclization/Bromination of 2-Alkynone O-Methyl Oximes in Ionic Liquid[J]. Chinese Journal of Organic Chemistry, 2019 , 39(5) : 1417 -1423 . DOI: 10.6023/cjoc201812006
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