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Synthesis method of phthalazine derivative

A synthesis method and technology of derivatives, applied in the field of chemistry, can solve the problems of toxic metals, large catalyst loading, cumbersome post-treatment process, etc., and achieve the effects of easy recovery, low cost and good application prospects.

Inactive Publication Date: 2012-07-11
SOUTHWEST UNIVERSITY
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

The synthesis of phthalazine derivatives reported in the literature is mostly supported by p-toluenesulfonic acid, sulfuric acid, silicotungstic acid, phosphotungstic acid, silanesulfonic acid, trimethylchlorosilane, polyphosphoric acid supported by silica, silica supported Phosphomolybdic acid, N, N, N', N'-tetrabromobenzene-1,3-disulfonamide, polyN-bromo-N -Ethylbenzene-1,3-disulfonamide, etc. are used as catalysts. Recently, there are reports in the literature that cerium sulfate is used to catalyze one-pot four-component synthesis of phthalazine derivatives, but these methods have unavoidable shortcomings. , such as the use of toxic metals, toxic or volatile solvents, expensive catalysts or large catalyst loadings, cumbersome post-treatment processes, difficult recovery of catalysts or solvents, etc.

Method used

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  • Synthesis method of phthalazine derivative
  • Synthesis method of phthalazine derivative
  • Synthesis method of phthalazine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1, the influence of catalyst type and loading

[0023] Ionic liquids (ILs) have recyclability and good solubility, not only as solvents but also as good catalysts. In this example, the reaction of phthalic hydrazide, dimedone and p-nitrobenzaldehyde was used as a template reaction, and the catalytic activity and loading of the ionic liquid were investigated. The experimental method is as follows: add phthalic hydrazide (1.0 mmol), dimedone (1.0 mmol) and p-nitrobenzaldehyde (1.2 mmol) to the reaction flask, without adding catalyst or adding the following ionic liquids as Catalyst: 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIm]BF 4 ), 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIm]PF 6 ), 1-butyl-3-methylimidazole acetate [BMIm]Ac, 1-butyl-3-methylimidazole hydrogen sulfate ([BMIm]HSO 4 ), 1-butylsulfonic acid-3-methylimidazole hydrogen sulfate ([BSO 3 HMIm]HSO 4 ), then 1 ml of PEG 600 was added, and the reaction temperature was controlled ...

Embodiment 2

[0028] Embodiment 2, the influence of reaction solvent and reaction temperature

[0029] In this example, the reaction of phthalic hydrazide, dimedone and p-nitrobenzaldehyde is used as a template reaction, and [BSO 3 HMIm]HSO 4 As the catalyst, the reaction solvent and reaction temperature were investigated. The experimental method is: add phthalic hydrazide (1.0 mmol), dimedone (1.0 mmol), p-nitrobenzaldehyde (1.2 mmol) and [BSO] into the reaction flask 3 HMIm]HSO 4 (0.15 mmol), then added solvent, and the reaction was carried out under temperature control for 30 minutes. The post-processing method was the same as that in Example 1. The results are shown in Table 2.

[0030] Table 2 Influence of reaction solvent and temperature

[0031]

[0032]It can be seen from Table 2 that (1) using water or ethanol as a solvent, the yield of reflux reaction for 30 minutes is very low, while using PEG 600 as a solvent, the yield of reaction at 120° C. for 30 minutes reaches 81%...

Embodiment 3

[0033] Embodiment 3, the influence of the molar ratio of substrate feeding

[0034] This embodiment takes the reaction of phthalic hydrazide, dimedone and p-nitrobenzaldehyde as a template reaction, and [BSO 3 HMIm] HSO 4 As a catalyst, the molar ratio of substrate to feed was investigated. The experimental method is: add phthalic hydrazide (1.0mmol), dimedone (1.0~1.5mmol), p-nitrobenzaldehyde (1.2~1.7mmol) and [BSO 3 HMIm] HSO 4 (0.15 mmol), and then add 1ml PEG 600, and react at a temperature of 120°C for 30 minutes, and the post-treatment method is the same as in Example 1. The results are shown in Table 3.

[0035] Table 3 The effect of substrate molar ratio

[0036]

[0037] As can be seen from Table 3, along with the increase of the molar ratio of phthalic hydrazide, dimedone and p-nitrobenzaldehyde, the productive rate increases gradually, and when the molar ratio of the three reaches 1:1.4:1.6, the productive rate is the highest Reach 95%, continue to incre...

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Abstract

The invention discloses a synthesis method of a phthalazine derivative. In the method, phthalylhydrazine and dimedone or 1,3-cyclohexanedione react with aromatic aldehyde or aliphatic aldehyde in the conditions that the ionic liquid [BSO3HMIm]HSO4 is used as a catalyst, PEG (polyethylene glycol) 600 is used as a solvent and the temperature is 100-160 DEG C; and the phthalazine derivative is synthesized from three components in one pot. The synthesis method has the advantages of low cost, good application prospect and the like, and is efficient, non-toxic and environment-friendly; and the catalyst and solvent are easily recycled and can be recycled.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to a synthesis method of a class of compounds. Background technique [0002] Compared with traditional linear synthesis reactions, multicomponent synthesis reactions have the advantages of low cost, short time, atom economy, and environmental friendliness, and can synthesize novel and complex molecular structures in one step, which has attracted more and more attention in recent years. [0003] Heterocyclic compounds are ubiquitous in nature and are closely related to people's lives. Phthalazine derivatives belong to heterocyclic compounds, which have various biological activities such as antispasmodic, cardiotonic, vascular relaxation, anticytotoxic, antibacterial, anti-inflammatory, anticancer, and have the potential to be used as fluorescent materials. The synthesis of phthalazine derivatives reported in the literature is mostly supported by p-toluenesulfonic acid, sulfuric acid, silicotun...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 官智何延红宋世铧
Owner SOUTHWEST UNIVERSITY
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