Introduction of an isoxazoline unit to the β-position of porphyrin via regioselective 1,3-dipolar cycloaddition reaction

被引:5
|
作者
Liu, Xiujun [1 ,2 ]
Ma, Xiang [1 ]
Feng, Yaqing [2 ,3 ]
机构
[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Res Ctr Anal & Test, Meilong Rd 130, Shanghai 200237, Peoples R China
[2] Tianjin Univ, Sch Chem Engn & Technol, Tianjin 300072, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷
基金
中国国家自然科学基金;
关键词
dipolar cycloaddition; isoxazoline; macrocycles; nitrile oxide; porphyrin; FUSED CHLORINS; NITRILE OXIDES; CYCLOOXYGENASE-2; BACTERIOCHLORINS; DIPOLAROPHILES; INHIBITORS; NITRONES; DESIGN; ENERGY;
D O I
10.3762/bjoc.15.143
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isoxazoline-linked porphyrins have been synthesized by a regioselective 1,3-dipolar cycloaddition reaction between vinylporphyrin 2 and nitrile oxides. The steric interaction directed the reaction trajectory, in which only the product with a link between the 5-position of the isoxazoline and the beta-position of porphyrin was observed. The isoxazoline-porphyrins 3a, b have been characterized by absorption, emission, H-1 NMR and mass spectra. Later, the crystal structure of 3a was obtained and confirmed the basic features of the NMR-derived structure. Furthermore, a pair of enantiomers of 3a presented in the crystal, which formed a dimeric complex through intermolecular coordination between the Zn2+ center and the carbonyl group of the second molecule.
引用
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页码:1434 / 1440
页数:7
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