Quinazoline and quinazolinone compound, its synthesis method and application

A kind of quinazolinoquinazolinone, synthesis method technology, applied in quinazolinoquinazolinone compound and its synthesis, the field of nitrogen-containing heterocyclic compounds, can solve problems such as never involved

Inactive Publication Date: 2015-04-08
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] As mentioned above, although a variety of methods for the preparation of quinazolinones have been disclosed in the prior art, there are few reports on compounds containing quinazolinones and quinazoline fused skeletons at the same time, let alone their preparation method routes and methods. up
[0015] In addition, so far, all studies involving quinazolinones have focused on their pharmaceutical activity, and a large number of studies have been conducted on the therapeutic mechanism, activity, etc., but have never involved research on uses other than pharmaceutical activity.

Method used

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  • Quinazoline and quinazolinone compound, its synthesis method and application
  • Quinazoline and quinazolinone compound, its synthesis method and application
  • Quinazoline and quinazolinone compound, its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] (A) Preparation of compound (II)

[0067]

[0068] Add 10 mmol anthranilamide 1, 12 mmol 2-bromobenzaldehyde 2, 12 mmol citric acid and 10 ml ethanol into the reaction flask, and react under reflux and stirring at 80°C for 16 hours. After the reaction, use anhydrous MgSO 4 After drying, concentration under reduced pressure to remove ethanol, the residue was separated by 400 mesh silica gel column chromatography to obtain the target product (II) with a yield of 81.7%.

[0069] (B) Preparation of compound (I)

[0070]

[0071] In a reaction vessel equipped with a stirrer, a thermometer, and a feeding port, add 50 ml of solvent THF, and then add the above formula compounds (II), (III), Cu(acac) 2 And Cs 2 CO 3 , The molar ratio is 1:1:0.02:2, and the compound of formula (II) is 10 mmol. Replace with nitrogen for three times, and then react for 16 hours at 60°C with stirring under the protection of continuous nitrogen. After the reaction, the mixture was poured into ethyl acetat...

Embodiment 2

[0076] (A) Preparation of compound (II)

[0077]

[0078] Add 10mmol 2-amino-5-methylbenzamide 1, 12mmol 2-bromobenzaldehyde 2, 12mmol citric acid and 10ml ethanol into the reaction flask, and react under reflux and stirring at 80°C for 16 hours. After the reaction, use anhydrous MgSO 4 After drying, concentration under reduced pressure to remove ethanol, the residue was separated by 350 mesh silica gel column chromatography to obtain the target product (II) with a yield of 86.3%.

[0079] (B) Preparation of compound (I)

[0080]

[0081] In a reaction vessel equipped with a stirrer, a thermometer and a feeding port, add 50ml of solvent toluene, and then add the above formula compounds (II), (III), Cu(acac) 2 And Cs 2 CO 3 , The molar ratio is 1:2:0.05:3, and the compound of formula (II) is 10 mmol. Replace with nitrogen three times, and then react for 20 hours at 80°C with stirring under the protection of continuous nitrogen flow. After the reaction, the mixture was poured into et...

Embodiment 3

[0086] (A) Preparation of compound (II)

[0087]

[0088] Add 10mmol 2-amino-5-chlorobenzamide 1, 12mmol 2-bromobenzaldehyde 2, 12mmol citric acid and 10ml ethanol into the reaction flask, and react under reflux and stirring at 80°C for 16 hours. After the reaction, use anhydrous MgSO 4 After drying, concentration under reduced pressure to remove ethanol, the residue was separated by 400 mesh silica gel column chromatography to obtain the target product (II) with a yield of 82.5%.

[0089] (B) Preparation of compound (I)

[0090]

[0091] In a reaction vessel equipped with a stirrer, a thermometer and a feeding port, add 50ml of solvent dichloromethane, and then add the above formula compounds (II), (III), Cu(acac) 2 And Cs 2 CO 3 , The molar ratio is 1:3:0.08:4, wherein the compound of formula (II) is 10 mmol. Replace with nitrogen for three times, and then react for 24 hours at 90°C with stirring under the protection of continuous nitrogen. After the reaction, the mixture was pou...

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Abstract

The invention relates to a quinazoline and quinazolinone compound, its synthesis method and application. According to the synthesis method, a copper compound is taken as a catalyst. The quinazoline and quinazolinone compound is prepared by one step reaction of dihydroquinolinone and amidine compound. The synthesis method has advantages of mild reaction condition, high product yield, simple post-processing. Furthermore, the quinazoline and quinazolinone compound is surprisingly found that it has an obvious fluorescent intensity alteration characteristic, which can be used in the application field of fluorescence sensing and has wide application prospect and research value.

Description

Technical field [0001] The invention relates to a nitrogen-containing heterocyclic compound, in particular to a quinazolinoquinazolinone compound and its synthesis method and application, belonging to the field of organic chemistry. Background technique [0002] Polycyclic nitrogen-containing heterocyclic compounds widely exist in nature, and some of them are used in drug research because of their certain biological activity. For example, it has long been found that polycyclic compounds with quinazolinone as the skeleton exist in drugs that can be used as drugs. In the core structure of a variety of natural products, such as active compounds such as deoxyvasicinone, Luotonin A, Circumdatins, Rutaecarpine and Tryptanthrin in. Because polycyclic quinazolinone compounds have a variety of drug activities, such as anti-tumor, anti-bacterial, anti-fungal, anti-depressant, anti-inflammatory, anti-rheumatic, anti-hypertensive, anti-spasm, anti-malaria, anti-infection and analgesic, etc....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06G01N21/64
Inventor 陈久喜吴华悦刘妙昌高文霞黄小波陈锡安
Owner WENZHOU UNIV
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