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Method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis

A technology of benzopyran derivatives and functional ionic liquids, which is applied in the field of catalyzed preparation of benzopyran derivatives by choline chloride functional ionic liquids, can solve the problems of poor catalyst reusability, cumbersome post-treatment process, and low yield of target products. efficiency and other issues, to achieve the effect of good reusability, simple post-processing, and low price

Inactive Publication Date: 2013-08-07
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above methods have their own advantages, they generally have the following defects: cumbersome post-treatment process, long reaction time, low yield of target product, generation of a large amount of pollutants and poor catalyst reusability, etc.

Method used

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  • Method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis
  • Method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis
  • Method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add benzaldehyde (5mmol), malononitrile (6mmol), dimethyl ketone (6mmol), 5mL water, 0.25mmol ionic liquid [Ch][OMe] into a 50mL single-necked bottle, stir at 80°C for 1 hour for TLC detection, the raw material disappeared, filtered, and vacuum-dried the filter cake to obtain the product with a yield of 96% and a content of 99%. Confirmation of the resulting product structure: 1 H NMR (400MHz, DMSO-d 6 )(ppm):7.29-7.10(m,5H),7.03(br,s,2H),4.15(s,1H),2.51(br,s,3H),2.25(d,1H,J=16Hz), 2.08(d,1H,J=16Hz),1.05(s,3H),0.96(s,3H); 13 C NMR (100MHz, DMSO-d 6 )(ppm): 196.3, 163.2, 159.3, 145.6, 128.9, 127.9, 127.2, 121.1, 113.4, 60.1, 50.8.

[0025]

Embodiment 2

[0027] Add p-methoxybenzaldehyde (5mmol), malononitrile (6mmol), dimethyl ketone (6mmol), 5mL water, and 0.25mmol ionic liquid [Ch][OMe] into a 50mL single-necked bottle in sequence, and stir at 80°C for 3 After 1 hour TLC detection, the raw material disappeared, filtered, and vacuum dried the filter cake to obtain the product, with a yield of 98% and a content of 98%. Confirmation of the resulting product structure: 1 H NMR (400MHz, DMSO-d 6 )(ppm):7.05(d,2H,J=8.8Hz),6.93(br,s,2H),6.78(d,2H,J=8.8Hz),4.13(s,1H),3.75(s,3H ),2.48(br,s,2H),2.25(d,1H,J=16Hz),2.06(d,1H,J=16Hz),1.01(s,3H); 13 C NMR (100MHz, DMSO-d 6 )(ppm): 196.2, 162.8, 159.1, 158.6, 137.6, 128.6, 120.5, 114.5, 113.7, 59.5, 55.8, 50.7, 41.1, 35.6, 32.5, 29.1, 27.6.

[0028]

Embodiment 3

[0030] Add p-nitrobenzaldehyde (5mmol), malononitrile (6mmol), dimethyl ketone (6mmol), 5mL water, and 0.25mmol ionic liquid [Ch][O(t-Bu)] into a 50mL single-necked bottle in sequence, Stir at 60°C for 0.5 hour TLC detection, the raw material disappeared, filter, and vacuum dry the filter cake to obtain the product, the yield was 92%, and the content was 98%. Confirmation of the resulting product structure: 1 H NMR (400MHz, DMSO-d 6 )(ppm):8.17(d,2H,J=8.8Hz),7.52(d,2H,J=8.8Hz),7.15(br,s,2H),4.32(s,1H),2.52(br,s ,2H),2.23(d,1H,J=16Hz),2.09(d,1H,J=16Hz),1.03(s,3H),0.95(s,3H); 13 C NMR (100MHz, DMSO-d 6 )(ppm): 196.4, 163.7, 159.3, 153.1, 146.8, 129.3, 124.3, 120.1, 113.1, 57.8, 50.3, 40.7, 36.6, 32.6, 28.9, 27.5.

[0031]

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PUM

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Abstract

The invention discloses a method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis. The method comprises the following steps of: carrying out catalytic condensation reaction on aromatic aldehyde, an active methylene compound and ketene dimethyl under normal pressure to obtain the benzopyran derivative by using the functional ion liquid based on choline chloride as the catalyst. The method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis is simple to operate, high in yield, good in reusability of catalytic reaction system, gentle in reaction condition and good in industrial prospect.

Description

technical field [0001] The invention relates to an efficient and green method for preparing benzopyran derivatives by "one-pot cooking" condensation reaction using choline chloride functional ionic liquid as a catalyst. Background technique [0002] Benzopyran derivatives can be used as degradable pesticide chemicals, photosensitive materials and cosmetics, etc., and have a very wide range of biological activities (document Eur.J.Med.Chem.1993,28,517-520.), and can be used as drugs Heal AIDS and Parkinson's syndrome, etc. At present, the method of synthesizing benzopyran products is a "one-pot" reaction method, and the catalyst includes 1,4-diazabicyclo[2.2.2]octane, N-methylimidazole, tetra-methyl ammonium hydroxide, (NH4) 2 HPO 4 、K 3 PO 4 , ZnO-beta zeolite, nanosized Ce 1 wxya 1 -XO 2 , Ru(II)complex, Na 2 SeO 4 , S-proline, L-proline, 1,8-diazabicyclo[5.4.0]undec-7-ene, sulfonic acid functionalized silica, phenylboronic acid, caro’s acid-silica gel and cerium(I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/74
Inventor 应安国杨健国邱方利王云龙马栋
Owner TAIZHOU UNIV
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