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Microwave-assisted synthesis method for ruthenium (II) arene compound

A technology for synthesizing aromatic hydrocarbons and microwave assisted, applied in the field of microwave assisted chemical synthesis, can solve problems such as low reaction yield, and achieve the effects of shortening reaction time, improving reaction yield and huge application value

Inactive Publication Date: 2013-01-30
广州鲁比生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the above synthesis method, it is often necessary to reflux the reaction raw materials in the solvent for several hours or even several days, and the reaction yield is relatively low

Method used

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  • Microwave-assisted synthesis method for ruthenium (II) arene compound
  • Microwave-assisted synthesis method for ruthenium (II) arene compound
  • Microwave-assisted synthesis method for ruthenium (II) arene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] PIP, a phenanthroimidazole derivative, has the following structural formula:

[0050]

[0051] Its microwave-assisted synthesis method is: o-phenanthroline-5,6-dione (315mg, 1.50mmol), benzaldehyde (238.5mg, 2.25mmol), ammonium acetate 4.5g, glacial acetic acid 20mL in a microwave reaction tube, 100 Microwave radiation at ℃ for 20 minutes; after the reaction, pour the reaction solution into 27 mL of distilled water, adjust the pH value to 7 with concentrated ammonia water under stirring, a large amount of precipitation was obtained, filtered, and dried to obtain a yellow crude product with a yield of 93.8% and a melting point of 320 ~323℃; ESI-MS(in EtOH, m / z): Experimental value: 297.4 (theoretical value: 297.1); IR (KBr pellet) ν: 3064, 2965, 2839, 1602, 1563, 1477, 1459, 1350 , 1046, 951, 875, 808, 739, 704 cm -1 ; UV-vis (EtOH): 225nm, 274nm, 289nm.

Embodiment 2

[0053] Phenanthroimidazole Derivatives o -MOPIP, its structural formula is as follows:

[0054]

[0055] O-phenanthroline-5,6-dione (315mg, 1.50mmol), 2-methoxybenzaldehyde (306mg, 2.25mmol), ammonium acetate 4.5g, glacial acetic acid 20mL in a microwave reaction tube, microwave at 100°C Irradiate for 20 minutes; after the reaction, pour the reaction solution into 27 mL of distilled water, adjust the pH value to 7 with concentrated ammonia water under stirring, a large amount of precipitation is obtained, filter, and dry to obtain a yellow crude product with a yield of 92.7%. Melting point 270~274℃; ESI-MS(in EtOH, m / z): Experimental value: 327.4 (theoretical value: 327.1); IR (KBr pellet) v: 3081, 2977, 1603, 1554, 1484, 1458, 1382 , 1043, 871, 815, 733, 698 cm -1 ; UV(EtOH): 225nm, 276nm, 290nm.

Embodiment 3

[0057] Phenanthroimidazole Derivatives m -MOPIP, its structural formula is as follows:

[0058]

[0059] O-phenanthroline-5,6-dione (315mg, 1.50mmol), 3-methoxybenzaldehyde (306mg, 2.25mmol), ammonium acetate 4.5g, glacial acetic acid 20mL in a microwave reaction tube, microwave at 100°C Irradiate for 20 minutes; After the reaction, pour the reaction solution into 27 mL of distilled water, adjust the pH value to 7 with concentrated ammonia water under stirring, a large amount of precipitation is obtained, filter, and dry to obtain a yellow crude product with a yield of 91.3%. Melting point 269~273°C; ESI-MS (in EtOH, m / z): experimental value: 327.4 (theoretical value: 327.1); IR (KBr pellet) v: 3087, 2972, 1598, 1561, 1481, 1456, 1376, 1032, 863, 805, 726, 714 cm -1 ; UV(EtOH): 225nm, 274nm, 289nm.

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Abstract

The invention discloses a microwave-assisted synthesis method for a ruthenium (II) arene compound. The method comprises the following steps: adding a ruthenium (II) arene precursor, a phenanthrene imidazole derivative and dichloromethane to a reaction tube; introducing nitrogen into the microwave reaction tube; carrying out a microwave irradiation reaction at a temperature of 50 to 70 DEG G for 0.5 to 30 min; and after the reaction is finished, drying a reaction mixture through spinning, adding water for dissolution, carrying out filtration, drying mother liquor through spinning and carrying out re-crystallization. The microwave-assisted synthesis method for the ruthenium (II) arene compound provided by the invention has the advantages of high efficiency and high yield; compared with traditional heating methods, the method provided by the invention enables reaction time to be greatly shortened and reaction yield to be improved; and the method has a great application value in synthetic chemistry and industrial production.

Description

technical field [0001] The invention belongs to the field of microwave-assisted chemical synthesis, in particular to a method for microwave-assisted synthesis of aromatic hydrocarbon ruthenium (II) compounds. Background technique [0002] Microwave-assisted chemical synthesis as a green synthesis technology can make those reactions that originally took hours or even days to complete can now be realized in minutes or even tens of seconds (Acc. Chem. Res., 2005, 38 , 653-661; Microwave in Organic and Medicinal Chemistry, Kappe and Stadler, Sweden, 2007, 1). Himeda, Y. et al. in Organometallics (2004, 23, 1480-1483) discloses the synthesis of arene ruthenium(II) compounds of the following structure. [0003] [0004] In Sptephicka, P et al in Inorgnanica Chimica Acta (359,2369-2374 (2006) disclose the synthesis of the following compounds and their corresponding aqueous complexes, in Canivet, J. et al in J.Organomet.Chem.( 2005, 690, 3202-3211) reported their synthesis met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07D471/14
Inventor 梅文杰吴琼
Owner 广州鲁比生物科技有限公司
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