Synthetic method of quinazolinone Schiff base compounds

A quinazolinone and a synthesis method technology are applied in the field of synthesizing quinazolinone Schiff base compounds, and can solve the problems of adding ligands, many reaction steps, high solvent toxicity, etc., so as to improve the reaction yield and simplify the The effect of simple and easy reaction steps and preparation methods

Active Publication Date: 2017-03-08
SHAANXI UNIV OF SCI & TECH
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Existing synthetic methods about quinazolinone Schiff base compounds mostly adopt anthranilic hydrazide and aldehyde compounds as reaction substrates to synthesize. These synthetic methods have their advantages, but there ar...

Method used

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  • Synthetic method of quinazolinone Schiff base compounds
  • Synthetic method of quinazolinone Schiff base compounds
  • Synthetic method of quinazolinone Schiff base compounds

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preparation example Construction

[0053] A kind of preparation method of quinazolinone Schiff base compound, synthetic route is as follows:

[0054]

[0055] R is H or Cl, R 1 and R 2 Selected from independent H, C1-C6 alkyl, benzyl, aromatic groups with different substituents, aromatic groups with different substituents include unsubstituted aryl, unsubstituted heteroaryl, aromatic with substituents A group or a heteroaryl group with substituents, the substituents are independently selected from C1-C6 alkyl, C1-C6 alkoxy.

[0056] Include the following steps:

[0057] Step 1: Weigh isatoic anhydride (as shown in formula I), carbonyl-containing compound (aromatic aldehyde, heterocyclic aromatic aldehyde or cyclic compound containing carbonyl in the molar ratio of 1:(2-2.2):1, such as formula III) and hydrazine hydrate (as shown in formula II) as raw materials;

[0058]Step 2: After mixing the raw materials weighed in step 1 in a solvent (ethanol, DMSO, DMF, Dioxane, NMP, water, or a mixed solvent obtain...

Embodiment 1

[0062] Preparation of 2-phenyl-3-(benzylideneamino)-4(1H)-quinazolinone

[0063] Dissolve 1 mmol of isatoic anhydride in ethanol and water mixed solution solvent with a volume ratio of 1:3, add 2.2 mmol of benzaldehyde and 1 mmol of hydrazine hydrate, use 0.15 mmol of nano-copper oxide as a catalyst, and heat at reflux at 76 ° C for 5 Hour, monitor the progress of reaction with TLC, concentrate after the reaction is complete, separate through column chromatography, obtain 271mg light yellow solid, productive rate is 83%, and gained product structural formula is as follows:

[0064]

[0065] Such as figure 1 with figure 2 Shown, product NMR characterization: 13 C NMR(101MHz,DMSO)δ160.74(s,1H),151.19(s,2H),146.16(s,1H),139.99(s,1H),134.48(s,1H),134.04(s,2H) ,130.40(s,2H),128.77(s,4H),128.53–127.95(m,9H),127.29(s,5H),126.31(s,5H),117.81(s,2H),114.75(d,J =11.4Hz,4H),71.70(s,2H). 13 C NMR (101MHz, DMSO) δ160.74, 151.19, 146.16, 139.99, 134.48, 134.04, 130.40, 128.77, 128.4...

Embodiment 2

[0067] Preparation of 2-phenyl-3-(4'-formyl-benzylideneamino)-4(1H)-quinazolinone

[0068] Dissolve 1mmol of isatoic anhydride in ethanol and water mixture solvent with a volume ratio of 1:2.5, add 2mmol of terephthalaldehyde and 1mmol of hydrazine hydrate, use 0.1mmol of nano-cerium oxide as a catalyst, and heat to reflux at 80°C After 6 hours, the reaction was monitored by TLC. After the reaction was complete, it was concentrated and separated by column chromatography to obtain 268 mg of a light yellow solid with a yield of 70%. The structural formula of the product obtained was as follows:

[0069]

[0070] Such as image 3 with Figure 4 Shown, product NMR characterization: 1 H NMR(400MHz,DMSO)δ10.04(s,1H),9.94(s,1H),9.00(s,1H),8.11(t,J=3.8Hz,1H),8.01–7.84(m,6H) ,7.74(dd,J=7.8,1.0Hz,1H),7.59(d,J=8.2Hz,2H),7.37–7.29(m,1H),6.86–6.68(m,3H). 13 C NMR (101MHz, DMSO) δ192.73, 192.54, 160.68, 148.95, 146.13, 145.95, 139.94, 137.00, 136.06, 134.44, 129.91, 129.75, 128.25, 1...

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Abstract

The invention discloses a synthetic method of quinazolinone Schiff base compounds. The synthetic method comprises the following steps: 1, raw materials including isatoic anhydride, carbonyl containing compounds and hydrazine hydrate are weighed in the mole ratio being 1:(2-2.2):1; 2, the raw materials weighed in the step 1 are mixed in a solvent, and the mixture is subjected to a heating reflux reaction with a nanometer metal oxide as a catalyst; 3, reaction products obtained in the step 2 are separated and purified, and the quinazolinone Schiff base compounds are obtained. With the adoption of the synthetic method, poisonous solvents and acid and alkaline conditions used in current synthetic reactions are avoided, reaction steps are reduced, and the reaction yield is increased.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing quinazolinone Schiff base compounds. Background technique [0002] Quinazolinones are important nitrogen-containing heterocyclic compounds. About 150 alkaloids isolated from natural products have quinazolinone ring skeletons. These compounds have shown good activities in anti-inflammatory, antibacterial, antihypertensive, diuretic, analgesic and other aspects. Quinazolinone Schiff bases are an important class of quinazolinone derivatives, and their synthesis methods have also attracted widespread attention. The existing synthetic methods of quinazolinone Schiff base compounds mostly use anthranilhydrazide and aldehyde compounds as reaction substrates for synthesis. These synthetic methods have their advantages, but there are also certain deficiencies. For example, there are many reaction components, the reaction must be carried out under acidic or alka...

Claims

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Application Information

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IPC IPC(8): C07D239/92C07D401/14C07D239/70C07D405/14
CPCC07D239/70C07D239/92C07D401/14C07D405/14
Inventor 张金程佩马养民刘佳马宇强
Owner SHAANXI UNIV OF SCI & TECH
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