One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI

doi:10.6023/cjoc201611020

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 954-958.DOI: 10.6023/cjoc201611020 Previous Articles Next Articles

ARTICLE

CuI催化无溶剂一锅法合成苯二氮?酮类化合物

张青扬, 汪小涧, 肖琼, 尹大力

北京协和医学院&中国医学科学院药物研究所天然药物活性物质与功能国家重点实验室活性物质发现与适药化研究北京重点实验室北京 100050

收稿日期:2016-11-18 修回日期:2016-12-14 发布日期:2017-01-04
通讯作者: 尹大力 E-mail:yindali@imm.ac.cn

One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI

Zhang Qingyang, Wang Xiaojian, Xiao Qiong, Yin Dali

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050

Received:2016-11-18 Revised:2016-12-14 Published:2017-01-04
Contact: 10.6023/cjoc201611020 E-mail:yindali@imm.ac.cn

1. One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI.PDF(1708KB)

Abstract

Benzodiazepinones are the important class of organic heterocyclic compounds with physiological activities. Herein, one pot procedure for the synthesis of benzodiazepinones has been developed under solvent-free condition. The substituted ethyl 2-bromobenzoates were cross-coupled with adjacent diamine compounds using CuI as a catalyst to give the intermediates, which spontaneously underwent an intramolecular N-acylation producing corresponding benzodiazepinones. This method has the advantages of enviroment frendly, mild reaction conditions, simple one pot operation and high yields. Under the optimized conditions, the effect of various substituted group on the reaction was investigated and the tolerance of this system was evaluated. This protocol could tolerate a variety of functional groups, and provide efficient access to a wide variety of substituted benzodiazepinones in good yields, including biological active molecules.

Key words: solvent-free, one pot, CuI, benzodiazepinones, catalyzed-coupling reaction

Cite this article

Zhang Qingyang, Wang Xiaojian, Xiao Qiong, Yin Dali. One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI[J]. Chin. J. Org. Chem., 2017, 37(4): 954-958.

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CuI催化无溶剂一锅法合成苯二氮?酮类化合物

One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI

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