Chinese Journal of Organic Chemistry >
Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives
Received date: 2016-05-16
Revised date: 2016-06-14
Online published: 2016-08-12
Supported by
Project supported by the National Natural Science Foundation of China (Nos. U1202221, 21362042), the Talent Found in Yunnan Province (No. 2012HB001), and the Excellent Young Talents of Yunnan University (No. XT412003).
In this article, a one-pot protocol was established for the synthesis of ketopiperazine-substituted quinone derivatives. This method based on the building blocks of piperazine ketone enamine ester 1, which reacted with quinones 2 through α-C selective alkylation of the enamine ester and via dehydrogenation oxidation reaction in acetonitrile at room temperature and acetic acid as catalyst. As a result, a series of novel ketopiperzine-substituted quinone derivatives 3a~3l have been synthesized efficiently with 70%~88% yield. This method possesses some advantages such as simple synthetic route, readily available starting materials, high yields and simple work-up procedures.
Key words： enamine ester; ketopiperzine; quinone derivatives; acetic acid; selective alkylation
Yang Ruixia , Zhao Yucheng , Jiang Meiyu , Yan Shengjiao , Lin Jun . Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives[J]. Chinese Journal of Organic Chemistry, 2016 , 36(12) : 2941 -2947 . DOI: 10.6023/cjoc201605025
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