Zn/Y Bimetallic Relay Catalysis: One Pot Intramolecular Cyclo-isomerization/Intermolecular Alder-Ene Reaction toward Oxazole α-Hydroxy Amide Derivatives

doi:10.6023/cjoc201909002

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 704-713.DOI: 10.6023/cjoc201909002 Previous Articles Next Articles

Zn/Y双金属接力催化:一锅法分子内环异构化/分子间阿尔德-烯反应构建α-羟基酰胺噁唑衍生物

张硕^a, 楼建芳^b, 王佳睿^c, 宋子贺^b, 彭丹^a, 王峰^a, 闫志旺^b, 崔仕麒^b, 刘一帆^b, 牟秋红^a, 李金辉^a

a 齐鲁工业大学(山东省科学院)山东省科学院新材料研究所山东省特种含硅新材料重点实验室济南 250014;
b 齐鲁工业大学(山东省科学院)化学与制药工程学院济南 250353;
c 山东农业大学食品科学与工程学院山东泰安 271018

收稿日期:2019-09-02 修回日期:2019-10-23 发布日期:2019-11-07
通讯作者: 楼建芳 E-mail:jianfanglou@126.com
基金资助:
山东省自然科学基金（No.ZR2017BB033）、山东省科学院青年基金（No.2018QN0030）、国家自然科学基金（No.51503118）资助项目.

Zn/Y Bimetallic Relay Catalysis: One Pot Intramolecular Cyclo-isomerization/Intermolecular Alder-Ene Reaction toward Oxazole α-Hydroxy Amide Derivatives

Zhang Shuo^a, Lou Jianfang^b, Wang Jiarui^c, Song Zihe^b, Peng Dan^a, Wang Feng^a, Yan Zhiwang^b, Cui Shiqi^b, Liu Yifan^b, Mu Qiuhong^a, Li Jinhui^a

a Shandong Provincial Key Laboratory for Special Silicone-Containing Materials, Advanced Materials Institute, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014;
b School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353;
c College of Food Science and Engineering, Shandong Agricultural University, Taian 271018

Received:2019-09-02 Revised:2019-10-23 Published:2019-11-07
Supported by:
Project supported by the Shandong Provincial Natural Science Foundation (No. ZR2017BB033), the Youth Science Funds of Shandong Academy of Sciences (No. 2018QN0030) and the National Natural Science Foundation of China (No. 51503118).

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Abstract

A novel tandem metal relay catalytic system of Zn/Y has been successfully developed. By using this unprecedented Zn(OTf)₂/Y(OTf)₃ bimetallic relay catalytic system, a variety of oxazole α-hydroxy amides derivatives were obtained from easily available N-(propargyl)-arylamides and various 1-benzylindoline-2,3-dione derivatives through intramolecular cycloisomerization/intermolecular Alder-ene reaction under mild conditions. The first step of the one-pot procedure is that Zn(OTf)₂ acts as a π acid to activate the triple bond of N-(propargyl)-arylamides, and a subsequent intramolecular 5-exo-dig cyclization forms the oxazoline intermediate. Separately, Y(OTf)₃ acts as Lewis acid, then oxazoline intermediate and 1-benzylindoline-2,3-dione derivatives are transformed to the oxazole α-hydroxy amide derivatives in good to excellent yields in an intermolecular Alder-ene reaction. Control experiments in the optimization section disclose the fact that Zn(OTf)₂ and Y(OTf)₃ are both indispensable for this intramolecular cycloisomerization/intermolecular Alder-ene reaction. Generally, the synthetic reactions run under air atmosphere by heating all the substrates and reagents in one-pot at 100℃. The present method benefits from the distinctive features of simple reaction conditions, high atom economy and broad substrate tolerance. It is of great significance for the synthesis of oxazole derivatives.

Key words: relay catalysis, cycloisomerization, Alder-Ene reaction, oxazole derivatives

Cite this article

Zhang Shuo, Lou Jianfang, Wang Jiarui, Song Zihe, Peng Dan, Wang Feng, Yan Zhiwang, Cui Shiqi, Liu Yifan, Mu Qiuhong, Li Jinhui. Zn/Y Bimetallic Relay Catalysis: One Pot Intramolecular Cyclo-isomerization/Intermolecular Alder-Ene Reaction toward Oxazole α-Hydroxy Amide Derivatives[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 704-713.

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Zn/Y双金属接力催化:一锅法分子内环异构化/分子间阿尔德-烯反应构建α-羟基酰胺噁唑衍生物

Zn/Y Bimetallic Relay Catalysis: One Pot Intramolecular Cyclo-isomerization/Intermolecular Alder-Ene Reaction toward Oxazole α-Hydroxy Amide Derivatives

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