Method for preparing phenazine compound by catalyzing o-halogeno aniline in water phase
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A technology of catalysts and in-situ catalysts, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve problems such as dangerous operation, difficult control, and many by-products
Inactive Publication Date: 2011-10-05
SICHUAN UNIV
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These methods have problems such as dangerous operation, difficulty in control, high reaction temperature, low yield, many by-products, difficulty in separation and purification, consumption of organic solvents, large amount of metal consumption, and serious environmental pollution.
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Embodiment 1
[0024] Example 1: Preparation of phenazine: 0.5 mmol (109.5 mg) of o-iodoaniline, 0.05 mmol (29.1 mg) of copper complex, 1 mmol (138 mg) of potassium carbonate, 0.1 mmol (64.4 mg), water 10 mL. at 120 o React in a C oil bath for 30 hours, cool to room temperature, extract the product with ethyl acetate, concentrate under reduced pressure, and purify the product by column chromatography to obtain a light yellow solid product with a yield of 78%. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.77-7.79 (m, 4H), 8.18-8.21 (m, 4H) ppm (eg figure 1 ); 13 C NMR (100MHz, CDCl 3 ): δ = 129.6, 130.4, 143.4 ppm (eg figure 2 ). MS (EI, m / z ): 180[M + ].
Embodiment 2
[0025] Example 2: Preparation of 2,7-dimethylphenazine: The preparation method is the same as in Example 1, except that 0.5 mmol (116.5 mg) of 2-iodo-4-methylaniline is added, and the yield is 82%. 1 H NMR (400 MHz, CDCl 3 ): δ = 2.66 (s, 6H), 7.67 (d, 2H), 8.00 (s, 2H), 8.13 (d, 2H) ppm; 13 C NMR (100 MHz, CDCl 3 ): δ = 22.2, 127.6, 128.9, 133.4, 140.7, 142.2, 143.1 ppm. MS (EI, m / z ): 208[M + ].
Embodiment 3
[0026] Example 3: Preparation of 1,3,6,8-tetramethylphenazine: the preparation method is the same as in Example 1, except that 0.5 mmol (123.5 mg) of 2-iodo-4,6-dimethylaniline is added, and the yield 84%. 1 H NMR (400 MHz, CDCl 3 ): δ = 2.60 (s, 6H), 2.90 (s, 6H), 7.49 (s, 2H), 7.89 (s, 2H) ppm; 13 C NMR (100 MHz, CDCl 3 ): δ =17.6, 22.1, 126.0, 132.3, 136.7, 139.8, 141.5, 142.5 ppm. MS (EI, m / z): 236[M + ].
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Abstract
The invention provides a method for preparing a phenazine compound by catalyzing o-halogeno aniline in a pure water phase. By using a water soluble coordination compound as a catalyst, the phenazine compound is prepared by efficiently catalyzing the o-halogeno aniline in the pure water phase. The invention provides a novel method for preparing the phenazine compound, which has the advantages of environment friendliness, simplicity and convenience for operation, safety, low price and high efficiency. Compared with the prior art, the method provided by the invention is not only applicable to a large quantity of functional groups but also has the advantages of simplicity in operation, high yield, single product, convenience for separation and purification, safety, low price and less pollution. The catalyst is as follows: (1) an in-situ catalyst formed by a copper salt and 2-pyridine carboxylic acid, and (2) a coordination compound.
Description
technical field [0001] The present invention relates to a process for preparing phenazine derivatives from o-halogenated anilines catalyzed in pure aqueous phase. Background technique [0002] Phenazine compounds are a large class of antibacterial and antitumor active substances in nature, which are condensed ring compounds containing two benzene rings and one pyrazine ring. Natural phenazine compounds have broad-spectrum antibacterial and antibacterial activities. They are not only used for the treatment of diseases such as leukemia, leprosy, atypical acid-fast bacilli, Mycobacterium tuberculosis and tuberculosis, but also against wheat take-all, rice wilt, etc. Pathogenic bacteria have a significant inhibitory effect, which has attracted more and more attention in the fields of medicine and agriculture (see: (a) Laville J, Voisard C, Keel C, et al. Proc Natl Acad Sci USA , 1992, 89: 1562-1566.(b) Haas D, Blumer C, Keel C. Curr Opin Biotechnol , 2000, 11: 290-297). Natu...
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