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

被引：1

作者：

Cai, Zhengjun ^{[1
]}

Gao, Jianbao ^{[2
]}

Li, Bai ^{[1
]}

Zhong, Yuan ^{[1
]}

Feng, Xing ^{[1
]}

Xue, Jijun ^{[3
]}

Jiang, Xianxing ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

[2] Shandong Hanxing Med Technol Co Ltd, Changyi 261312, Peoples R China

[3] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 38卷 / 05期

基金：

中国国家自然科学基金;

关键词：

tetrazine; axial chirality; the inverse electronic demand Diels-Alder reaction; cyclooctyne; ATROPOSELECTIVE SYNTHESIS; LIGANDS; DESIGN;

D O I：

10.6023/cjoc201712039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1138 / 1146

页数：9

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