Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives

doi:10.6023/cjoc201605025

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (12): 2941-2947.DOI: 10.6023/cjoc201605025 Previous Articles Next Articles

ARTICLE

哌嗪酮取代醌类衍生物的简便合成

杨瑞霞, 赵宇澄, 蒋美妤, 严胜骄, 林军

云南大学化学科学与工程学院教育部自然资源药物化学重点实验室昆明 650091

收稿日期:2016-05-16 修回日期:2016-06-14 发布日期:2016-08-12
通讯作者: 严胜骄, 林军 E-mail:yansj@ynu.edu.cn;linjun@ynu.edu.cn
基金资助:
国家自然科学基金（Nos. U1202221，21362042），云南省后备人才（No. 2012HB001），云南大学青年英才计划（No. XT412003）资助项目.

Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives

Yang Ruixia, Zhao Yucheng, Jiang Meiyu, Yan Shengjiao, Lin Jun

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091

Received:2016-05-16 Revised:2016-06-14 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

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Yang Ruixia, Zhao Yucheng, Jiang Meiyu, Yan Shengjiao, Lin Jun. Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives[J]. Chin. J. Org. Chem., 2016, 36(12): 2941-2947.

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哌嗪酮取代醌类衍生物的简便合成

Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives

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