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

A microwave-assisted synthesis of aromatic hydrocarbons, applied in the field of microwave-assisted chemical synthesis, can solve the problem of low reaction yield, achieve the effects of shortened reaction time, increased reaction yield, and great application value

Inactive Publication Date: 2015-07-01
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

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The structural formula of the phenanthrimidazole derivative PIP is as follows:

[0050]

[0051] The microwave-assisted synthesis method is: o-phenanthroline-5,6-dione (315mg, 1.50mmol), benzaldehyde (238.5mg, 2.25mmol), 4.5g ammonium acetate, 20mL glacial acetic acid in a microwave reaction tube, 100 Microwave radiation at ℃ for 20min; after the reaction, the reaction solution was poured into 27mL of distilled water, the pH value was adjusted to 7 with concentrated ammonia while stirring, a large amount of precipitate 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 tablet) 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] Phenanthrimidazole derivatives o -MOPIP, its structural formula is as follows:

[0054]

[0055] Phenanthroline-5,6-dione (315mg, 1.50mmol), 2-methoxybenzaldehyde (306mg, 2.25mmol), 4.5g ammonium acetate, 20mL glacial acetic acid in a microwave reaction tube, microwave at 100°C Irradiate for 20 min; after the reaction, pour the reaction solution into 27 mL of distilled water, adjust the pH value to 7 with concentrated ammonia while stirring, obtain a large amount of precipitate, 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 tablet) v: 3081, 2977, 1603, 1554, 1484, 1458, 1382 , 1043, 871, 815, 733, 698 cm -1 ; UV(EtOH): 225nm, 276nm, 290nm.

Embodiment 3

[0057] Phenanthrimidazole derivatives m -MOPIP, its structural formula is as follows:

[0058]

[0059] Phenanthroline-5,6-dione (315mg, 1.50mmol), 3-methoxybenzaldehyde (306mg, 2.25mmol), 4.5g ammonium acetate, 20mL glacial acetic acid 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 to 7 with concentrated ammonia under stirring, obtain a large amount of precipitate, filter, and dry to obtain a yellow crude product with a yield of 91.3%. Melting point: 269~273℃; ESI-MS (in EtOH, m / z): experimental value: 327.4 (theoretical value: 327.1); IR (KBr tablet) 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 Patents(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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