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Anthracycline bistriazole-copper tetrafluoroborate complex with catalytic 4-methoxyphenylboronic acid and preparation method thereof

An anthracycline bistriazole copper and methoxybenzene boronic acid technology is applied in the field of inorganic synthesis, can solve problems such as expensive palladium catalyst, and achieve the effects of being suitable for large-scale production, high purity and high reaction yield

Inactive Publication Date: 2016-06-29
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the palladium catalyst is relatively expensive. If the expensive palladium catalyst can be replaced by a cheap copper complex to realize the reaction process, it can not only save costs, but also is expected to be industrialized.

Method used

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  • Anthracycline bistriazole-copper tetrafluoroborate complex with catalytic 4-methoxyphenylboronic acid and preparation method thereof
  • Anthracycline bistriazole-copper tetrafluoroborate complex with catalytic 4-methoxyphenylboronic acid and preparation method thereof
  • Anthracycline bistriazole-copper tetrafluoroborate complex with catalytic 4-methoxyphenylboronic acid and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole (tatrz) ligand

[0030] Using the "one-pot method", in the polar solvent DMF, 9,10-dibromoanthracene, triazole, potassium carbonate and copper oxide were prepared under heating conditions; wherein 9,10-dibromoanthracene: three Azole: potassium carbonate: the molar ratio of copper oxide is 2:10:30:1;

[0031]

[0032] The reaction temperature was 150°C, and the reaction time was 12 hours.

Embodiment 2

[0034] Cu(BF 4 ) 2 and 1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole (tatrz) in a molar ratio of 1: 1;

[0035] tatrz (0.0624g, 0.2mmol) and Cu (BF 4 ) 2 (0.0691g, 0.2mmol) in H 2 O (6mL) and CH 3CN (4mL) was stirred in a mixed solvent at room temperature for half an hour and then filtered, and the filtrate was volatilized at room temperature to form yellow rod-shaped crystals analyzed by X-ray single crystal diffraction. Yield: 35% (calculated based on tatrz). Elemental analysis (C 36 h 28 B 2 CuF 8 N 12 o 2 ) Theoretical value (%): C, 48.16; H, 3.14; N, 18.72. Found: C, 48.15; H, 3.16; N, 18.69.

Embodiment 3

[0037] The crystal structure was determined by APEXIICCD single crystal diffractometer, using graphite monochromatized Mokα ray (λ=0.71073?) as the incident radiation, collecting diffraction points by ω-2θ scanning, and correcting the unit cell parameters by the least square method. The difference Fourier electron density map was solved for the crystal structure using software and corrected for Lorentz and polarization effects. All H atoms were synthesized by difference Fourier transform and determined by ideal position calculation. The detailed crystal determination data are shown in Table 1. Structural primitives see figure 1 , the three-dimensional structure of the complex see figure 2 .

[0038] Table 1. Crystallographic data of complex 1

[0039]

[0040]

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Abstract

The invention relates to an anthracycline bitriazole and copper fluoroborate complex with a 4-methoxyphenylboronic acid catalysis effect and a preparation method of the anthracycline bitriazole and copper fluoroborate complex, and discloses a preparation method of {[Cu(tatrz)2(H2O)2] (BF4)2} (1) (tatrz=1-[9-(1H-1, 2, 4-triazole-1-yl)anthracene-10-yl]-1H-1, 2, 4-triazole) and a potential application value of {[Cu(tatrz)2(H2O)2] (BF4)2} (1) (tatrz=1-[9-(1H-1, 2, 4-triazole-1-yl)anthracene-10-yl]-1H-1, 2, 4-triazole) for catalyzing coupled reaction of 4-methoxyphenylboronic acid. The complex is prepared by using a normal-temperature volatilization method comprising the step of volatilizing by stirring Cu(BF4)2 and tatrz at normal temperature. The invention further discloses application of {[Cu(tatrz)2(H2O)2] (BF4)2} (1) (tatrz=1-[9-(1H-1, 2, 4-triazole-1-yl)anthracene-10-yl]-1H-1, 2, 4-triazole) as a 4-methoxyphenylboronic acid coupled reaction catalyst.

Description

[0001] The present invention has been funded by the National Natural Science Foundation of China (21471113), the Tianjin Municipal Education Commission project (20140506), the Tianjin Normal University academic innovation promotion project for young and middle-aged teachers, and the Tianjin Higher Education Innovation Team Training Program (TD12-5038). technical field [0002] The invention belongs to the technical field of inorganic synthesis and relates to copper complex {[Cu(tatrz) 2 (H 2 O) 2 ](BF 4 ) 2 Preparation of}(1)(tatrz=1-[9-(1H-1,2,4-triazol-1-yl)anthracene-10-yl]-1H-1,2,4-triazole) Method and application as catalyst for coupling reaction of 4-methoxyphenylboronic acid. Background technique [0003] The study of highly selective synthesis catalyzed by transition metal complexes has been an active field. Reactions that are difficult to achieve with common synthetic means can sometimes be completed in one step using transition metal complexes under mild condi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08B01J31/22C07C41/30C07C43/205
CPCB01J31/1815B01J2231/4205B01J2531/0213B01J2531/16C07C41/30C07C2531/22C07F1/08C07C43/205
Inventor 王英
Owner TIANJIN NORMAL UNIVERSITY
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