Application of [4+2]Cycloaddition Reaction of Tetrazine with Cyclooctyne in the Construction of Pyridazine Structure with Axial Chirality

doi:10.6023/cjoc201712039

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1138-1146.DOI: 10.6023/cjoc201712039 Previous Articles Next Articles

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四嗪化合物与环辛炔的[4+2]环加成反应及其在构建轴手性哒嗪骨架中的应用

蔡正军^a, 高建保^b, 李白^a, 钟源^a, 丰幸^a, 薛吉军^c, 蒋先兴^a

a 中山大学药学院广州 510006;
b 山东汉兴医药科技有限公司昌邑 261312;
c 兰州大学化学化工学院兰州 730000

收稿日期:2017-12-27 修回日期:2018-01-29 发布日期:2018-02-11
通讯作者: 薛吉军,E-mail:jiangxx5@mail.sysu.edu.cn;蒋先兴,E-mail:xuejj@lzu.edu.cn E-mail:jiangxx5@mail.sysu.edu.cn;xuejj@lzu.edu.cn
基金资助:
国家自然科学基金（Nos.91413107，21432003）、“青年千人”计划及中央高校基本科研业务费专项资金（No.lzujbky-2014-61）资助项目.

Application of [4+2]Cycloaddition Reaction of Tetrazine with Cyclooctyne in the Construction of Pyridazine Structure with Axial Chirality

Cai Zhengjun^a, Gao Jianbao^b, Li Bai^a, Zhong Yuan^a, Feng Xing^a, Xue Jijun^c, Jiang Xianxing^a

a School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006;
b Shandong Hanxing Medical Technology Co., Ltd., Changyi 261312;
c College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000

Received:2017-12-27 Revised:2018-01-29 Published:2018-02-11
Contact: 10.6023/cjoc201712039 E-mail:jiangxx5@mail.sysu.edu.cn;xuejj@lzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 91413107, 21432003), the Thousand Young Talents Program and the Fundamental Research Funds for the Central Universities of China (No. lzujbky-2014-61).

1. Application of [4+2]Cycloaddition Reaction of Tetrazine with Cyclooctyne in the Construction of Pyridazine Structure with Axial Chirality.PDF(1472KB)

Abstract

The application of [4+2] cycloaddition reaction of tetrazine with cyclooctyne in the construction of pyridazine structure with axial chirality was studied. The inverse electronic demand Diels-Alder reaction of tetrazine bearing bulky groups with macrocyclic tension’s cyclooctyne could take place under catalyst-free conditions in dichloromethane. The reaction underwent a six-membered bridged transition state, gently release a molecule of nitrogen to get axial chiral pyridazine structure. The transformation of the reaction can be determined by the change of color. The reaction could get potential axial chiral pyridazine structure with high yiled (95%) under mild conditions.

Key words: tetrazine, axial chirality, the inverse electronic demand Diels-Alder reaction, cyclooctyne

Cite this article

Cai Zhengjun, Gao Jianbao, Li Bai, Zhong Yuan, Feng Xing, Xue Jijun, Jiang Xianxing. Application of [4+2]Cycloaddition Reaction of Tetrazine with Cyclooctyne in the Construction of Pyridazine Structure with Axial Chirality[J]. Chin. J. Org. Chem., 2018, 38(5): 1138-1146.

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四嗪化合物与环辛炔的[4+2]环加成反应及其在构建轴手性哒嗪骨架中的应用

Application of [4+2]Cycloaddition Reaction of Tetrazine with Cyclooctyne in the Construction of Pyridazine Structure with Axial Chirality

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