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

ABSTRACT: 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 ?-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.

SUBMITTER: Liu X

PROVIDER: S-EPMC6604739 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Liu Xiujun X Ma Xiang X Feng Yaqing Y

Beilstein journal of organic chemistry 20190628

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 structur ...[more]

PMID: 31293693

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