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

页码：1434 / 1440

页数：7