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Green catalysis preparation method for 14-aryl group-14 H-dibenzo [a, j] xanthene type derivative

A technology of xanthene and its derivatives, which is applied in the field of green preparation of 14-aryl-14H-dibenzo[a, can solve the problems that ionic liquids are not easy to biodegrade, use a large amount of ionic liquids, and the preparation price is high. Inexpensive, simple preparation process, good catalytic activity

Active Publication Date: 2014-10-01
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved in the present invention is to overcome the difficulty of biodegradation of the ionic liquid in the process of preparing 14-aryl-14H-dibenzo[a,j]xanthene derivatives by acidic ionic liquid in the prior art, The preparation price is higher, the ionic liquid is used in a large amount and the loss in recycling is also relatively large, and a Bronster acidic ionic liquid that is easy to biodegrade, has high acidity, is simple to prepare, and is cheap is provided as a green catalyst. Catalytic preparation method of 14-aryl-14H-dibenzo[a,j]oxanthene derivatives under solvent-free conditions

Method used

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  • Green catalysis preparation method for 14-aryl group-14 H-dibenzo [a, j] xanthene type derivative
  • Green catalysis preparation method for 14-aryl group-14 H-dibenzo [a, j] xanthene type derivative
  • Green catalysis preparation method for 14-aryl group-14 H-dibenzo [a, j] xanthene type derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 10mmol benzaldehyde, 20mmol 2-naphthol and 0.4mmol catalyst into a 50ml single-necked bottle equipped with a condenser. React at 110°C for 24 minutes, add 10ml of water to cool after the reaction, a large amount of solids precipitate out, crush the solids, let it stand, and filter with suction, after the obtained filter residue is dried, recrystallize with 95% ethanol aqueous solution, and obtain pure 14-phenyl -14H-dibenzo[a,j]xanthene, the yield is 92%. The filtrate (mainly catalyst and water) can be reused after removing water by rotary evaporation under reduced pressure at 110°C.

[0026] 14-Phenyl-14H-dibenzo[a,j]xanthene: m.p.184~185℃; 1 H NMR (400MHz, DMSO-d 6 ): δ=6.71(s, 1H), 6.94(t, J=7.5Hz, 1H), 7.12(t, J=7.5Hz, 2H), 7.42(t, J=7.1Hz, 2H), 7.55(d , J=8.6Hz, 2H), 7.59~7.63(m, 4H), 7.88~7.91(m, 4H), 8.69(d, J=8.6Hz, 2H)

Embodiment 2

[0028] Add 10mmol of 4-chlorobenzaldehyde, 20mmol of 2-naphthol and 0.4mmol of catalyst into a 50ml single-necked bottle equipped with a condenser. React at 110°C for 17 minutes, add 10ml of water to cool after the reaction, a large amount of solids are precipitated, crush the solids, let stand, and filter with suction, after the obtained filter residue is dried, recrystallize with 95% ethanol aqueous solution, and obtain pure 14-(4 -Chlorophenyl)-14H-dibenzo[a,j]xanthene, yield 95%. The filtrate (mainly catalyst and water) can be reused after removing water by rotary evaporation under reduced pressure at 110°C.

[0029] 14-(4-Chlorophenyl)-14H-dibenzo[a,j]xanthene: m.p.285~286℃; 1 H NMR (300MHz, DMSO-d 6 ): δ=6.74(s, 1H), 7.16(t, J=6.7Hz, 2H), 7.45~7.62(m, 10H), 8.64(d, J=7.6Hz, 2H), 8.90(d, J= 7.8Hz, 2H)

Embodiment 3

[0031] Add 10mmol of 4-methylbenzaldehyde, 20mmol of 2-naphthol and 0.5mmol of catalyst into a 50ml single-necked bottle equipped with a condenser. React at 110°C for 19 minutes, add 10ml of water to cool after the reaction, a large amount of solids are precipitated, crush the solids, let stand, and filter with suction, the obtained filter residue is dried and recrystallized with 95% ethanol aqueous solution, and after vacuum drying, pure 14-(4 -Methylphenyl)-14H-dibenzo[a,j]xanthene, yield 87%. The filtrate (mainly catalyst and water) can be reused after removing water by rotary evaporation under reduced pressure at 110°C.

[0032] 14-(4-methylphenyl)-14H-dibenzo[a,j]xanthene: m.p.227~228℃; 1 H NMR (300MHz, DMSO-d 6): δ=2.00(s, 3H), 6.59(s, 1H), 6.87(d, J=7.1Hz, 2H), 7.41~7.62(m, 8H), 7.86(t, J=2.6Hz, 4H) , 8.63 (d, J=8.6Hz, 2H)

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Abstract

The invention discloses a green preparation method for 14-aryl group-14 H-dibenzo [a, j] xanthene type derivative and belongs to the technical field of chemical material preparation. According to the preparation method, in preparation reaction, the molar ratio of aromatic aldehyde to 2-naphthol is 1 to 2; the molar weight of the catalyst is 3-5 % of aromatic aldehyde; the reaction temperature is 110 DEG C; the reaction time is 10-30 min; the preparation method comprises the following steps: after reaction, water is added for cooling; a great amount of solid materials are precipitated; the solid materials are grinded and stand still and then are subjected to suction filtration; the obtained filter residues are water-washed and dried and then an aqueous solution with 95% of ethyl alcohol is adopted for recrystallization; the pure 14-aryl group-14 H-dibenzo [a, j] xanthene type derivative is obtained after vacuum drying. Compared with other preparation methods using acidic ionic liquid as the catalyst, the preparation method has the advantages that the catalyst activity is good, the losses in recycling are less, the biological degradation is easy to realize, the whole preparation process is simple, convenient and economic and the industrialized mass production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and in particular relates to a green method for preparing 14-aryl-14H-dibenzo[a,j]xanthene derivatives. Background technique [0002] Many organic compounds containing pyran rings have important physiological and pharmacological activities, such as hypoglycemic, anti-allergic, anti-dysplasia, antibacterial, anti-cancer, etc., and are used to treat allergic tracheitis, etc. The xanthene derivatives contain a pyran ring structure, especially 14-aryl-14H-dibenzo[a,j]xanthene derivatives, which are the basic structural units of many natural products and are also synthetic An important intermediate for many complex organic compounds. The traditional method for synthesizing 14-aryl-14H-dibenzo[a,j]xanthene derivatives is to prepare them by condensation reaction of aldehyde and 2-naphthol under the catalysis of proton or Lewis acid. However, these methods have disadvantages such as t...

Claims

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Application Information

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IPC IPC(8): C07D311/78B01J31/02
CPCC07D311/78
Inventor 储昭莲张志敏吴胜华岳彩波
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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