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Method for efficient catalytic synthesis of 2H-indole [2,1-b] phthalazine-1,6,11(13H) triketone

A phthalazine, high-efficiency technology, applied in the field of ionic liquid catalysis, can solve the problems of ionic liquids that are not easily biodegradable, large amount of ionic liquids used, complicated post-processing, etc., and achieves easy industrialized large-scale production, less catalyst usage, and solvent utilization. high rate effect

Active Publication Date: 2015-09-02
ANHUI UNIVERSITY OF TECHNOLOGY
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Problems solved by technology

[0005] The purpose of the present invention is to overcome the difficult biodegradation of ionic liquid in the process of utilizing acidic ionic liquid to catalyze the synthesis of 2H-indole[2,1-b]phthalazine-1,6,11(13H)-trione in the prior art, The preparation price is high, the amount of ionic liquid used is large, the amount of loss in recycling is also large, and the post-treatment is complicated. However, an acidic ionic liquid with easy biodegradation, high acidity, and low amount of use and loss is provided. As a green catalyst, the method for catalytically synthesizing 2H-indole[2,1-b]phthalazine-1,6,11(13H)-trione under the condition of ethanol as solvent

Method used

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  • Method for efficient catalytic synthesis of 2H-indole [2,1-b] phthalazine-1,6,11(13H) triketone
  • Method for efficient catalytic synthesis of 2H-indole [2,1-b] phthalazine-1,6,11(13H) triketone
  • Method for efficient catalytic synthesis of 2H-indole [2,1-b] phthalazine-1,6,11(13H) triketone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 1mmol of benzaldehyde, 1mmol of phthalic hydrazide, 1mmol of 5,5-dimethyl-1,3-cyclohexanedione and 0.03mmol of acidic ionic liquid to 3ml of ethanol with stirring bar and condensation tube in a 25ml single-necked bottle. Heated to reflux for 8 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction, the resulting filter residue was washed with ethanol and dried in vacuo to obtain pure 3,4- Dihydro-3,3-dimethyl-13-phenyl-2H-indole[2,1-b]phthalazine-1,6,11(13H)-trione, the yield is 90%. The filtrate was directly added with benzaldehyde, phthalic hydrazide and 5,5-dimethyl-1,3-cyclohexanedione for repeated use.

[0023] 3,4-dihydro-3,3-dimethyl-13-phenyl-2H-indole[2,1-b]phthalazine-1,6,11(13H)-trione: m.p.204~206 ℃; IR (KBr): 2960, 1665, 1578cm -1 ; 1 H NMR (300MHz, CDCl 3 ): δ=1.25(s, 6H), 2.47(s, 2H), 3.21(...

Embodiment 2

[0025]Add 1mmol of o-chlorobenzaldehyde, 1mmol of phthalic hydrazide, 1mmol of 5,5-dimethyl-1,3-cyclohexanedione and 0.05mmol of acidic ionic liquid into a stirring bar filled with 5ml of ethanol and a 25ml single-necked bottle with a condenser tube. Heated to reflux for 17 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction, the resulting filter residue was washed with ethanol and dried in vacuo to obtain pure 3,4- Dihydro-3,3-dimethyl-13-(2-chlorophenyl)-2H-indole[2,1-b]phthalazine-1,6,11(13H)-trione, the yield is 86%. Add o-chlorobenzaldehyde, phthalic hydrazide and 5,5-dimethyl-1,3-cyclohexanedione directly to the filtrate for repeated use.

[0026] 3,4-Dihydro-3,3-dimethyl-13-(2-chlorophenyl)-2H-indole[2,1-b]phthalazine-1,6,11(13H)-trione : m.p.263~265℃; IR(KBr): 3056, 2954, 2892, 1661cm -1 ; 1 H NMR (300MHz...

Embodiment 3

[0028] Add 1mmol p-tolualdehyde, 1mmol phthalic hydrazide, 1mmol 5,5-dimethyl-1,3-cyclohexanedione and 0.05mmol acidic ionic liquid to 4ml ethanol with stirring In a 25ml single-necked bottle with a sub and a condenser tube. Heated to reflux for 22 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction, the resulting filter residue was washed with ethanol and vacuum dried to obtain pure 3,4- Dihydro-3,3-dimethyl-13-(4-methylphenyl)-2H-indole[2,1-b]phthalazine-1,6,11(13H)-trione, yield was 87%. Add p-tolualdehyde, phthalic hydrazide and 5,5-dimethyl-1,3-cyclohexanedione directly to the filtrate for repeated use.

[0029] 3,4-Dihydro-3,3-dimethyl-13-(4-methylphenyl)-2H-indole[2,1-b]phthalazine-1,6,11(13H)-tri Ketone: m.p.244~246℃; IR(KBr): 2895, 1662, 1652, 1602, 1599, 1496, 1084, 828, 791, 687, 627, 494cm -1 ; 1 H NM...

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Abstract

The invention discloses a method for efficient catalytic synthesis of 2H-indole [2,1-b] phthalazine-1,6,11(13H) triketone, and belongs to the technical field of ionic liquid catalysis. The molar ratio of aromatic aldehyde, phthalylhydrazine and 5,5-dimethyl-1,3-cyclohexanedione in synthesis reaction is 1 to 1 to 1; the molar quantity of an acidic ionic liquid catalyst is 3%-7% of used phthalylhydrazine; the volume dose of a reaction solvent based on milliliter is 3-5 times of the molar quantity of the phthalylhydrazine based on millimole; and the method comprises the following steps: carrying out reflux reaction for 8-30 minutes; ending reaction, cooling to a room temperature, and separating out a lot of solids; carrying out suction filtration, washing residues with ethanol, and drying in vacuum to obtain a product. Compared with a synthesis method employing other acidic ionic liquid catalysts, the method has the characteristics of being high in catalytic activity of the catalyst, good in biodegradability and relatively in low preparation cost; the overall synthesis process is simple and convenient to operate; and industrialized large-scale application is facilitated.

Description

technical field [0001] The invention belongs to the technical field of ionic liquid catalysis, and in particular relates to a method for efficiently catalytically synthesizing 2H-indole[2,1-b]phthalazine-1,6,11(13H)-trione. Background technique [0002] Heterocyclic compounds are ubiquitous in nature and closely related to people's lives, and have attracted great interest in the past few decades. Phthalazinone derivatives containing phthalazine structural units, such as 2H-indole [2,1-b] phthalazine-1,6,11(13H)-trione, have important pharmacological and biological activities, It can play anti-spasmodic, anti-fungal, anti-cancer, anti-cytotoxic effects. In addition, it also has the potential to prepare fluorescent materials. Such compounds are usually synthesized by a three-component one-pot reaction of phthalic hydrazide, cyclohexanedione and aldehydes, but the traditional inorganic or organic acid catalysts commonly suffer from long reaction times, insufficient yields, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 储昭莲严珍吴胜华黄蕾岳彩波
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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