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

Beilstein Journal of Organic Chemistry

Xiang Ma¹  Xiujun Liu¹  Yaqing Feng² 

[1] Research Center of Analysis and Test, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Meilong Road 130, Shanghai 200237, China;School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;

关键词: dipolar cycloaddition;    isoxazoline;    macrocycles;    nitrile oxide;    porphyrin;   

DOI  :  10.3762/bjoc.15.143

来源: DOAJ

【 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 β-position of porphyrin was observed. The isoxazoline-porphyrins 3a,b have been characterized by absorption, emission, 1H 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.

【 授权许可】

Unknown