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Method for synthesizing quinazolino indazole derivatives under acidic condition

A synthetic method, quinazolinone technology, applied in the field of organic chemical synthesis, can solve the problem of many components, and achieve the effects of high product yield, high purity, good scientific research value and application prospect

Inactive Publication Date: 2014-08-13
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] This method can obtain the target product in one step, but there are many components in the reaction system: catalysts, alkalis and molecular sieves are required, and

Method used

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  • Method for synthesizing quinazolino indazole derivatives under acidic condition
  • Method for synthesizing quinazolino indazole derivatives under acidic condition
  • Method for synthesizing quinazolino indazole derivatives under acidic condition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: 5-phenylindazol[3,2-b]quinazolin-7(5H)-one

[0050]

[0051] 50ml solvent acetic acid is added in the reaction vessel, then add 10mmol (II) compound, 0.5mmol Pd(OAc) 2 , 30mmol of silver acetate, under the stirring of the stirring bar, heat up to 80 ℃ and seal the reaction for 48 hours.

[0052] After the reaction finished, the reaction mixture was cooled to room temperature, transferred to a separatory funnel, added ethyl acetate that was 3-5 times the volume of the mixture, and then added a 20% aqueous sodium hydroxide solution to adjust the pH value of the system to Alkaline, liquid separation, the organic layer was washed 1-3 times with saturated brine, and then rotatively evaporated, and the residue was passed through a 300-400 mesh silica gel column with ethyl acetate / petroleum ether as the eluent, in which ethyl acetate and petroleum The volume ratio of ether was 1:5, and the target product formula (I) compound 5-phenylindazol[3,2-b]quinazolin-7(5H...

Embodiment 2

[0056] Example 2: 5-p-tolyl indazol[3,2-b]quinazolin-7(5H)-one

[0057]

[0058] Add 50ml of solvent acetic acid to the reaction vessel, then add 10mmol of (II) compound, 1mmol of Pd(OAc) 2 , 40mmol silver acetate, under the stirring of the stirring bar, heat up to 90 ℃ and seal the reaction for 40 hours.

[0059] After the reaction finished, the reaction mixture was cooled to room temperature, transferred to a separatory funnel, added ethyl acetate that was 3-5 times the volume of the mixture, and then added a 20% aqueous sodium hydroxide solution to adjust the pH value of the system to Alkaline, liquid separation, the organic layer was washed 1-3 times with saturated brine, and then rotatively evaporated, and the residue was passed through a 300-400 mesh silica gel column with ethyl acetate / petroleum ether as the eluent, in which ethyl acetate and petroleum The volume ratio of ether was 1:10, and the target product formula (I) compound 5-p-tolyl indazol[3,2-b]quinazolin-...

Embodiment 3

[0063] Example 3: 5-p-trifluorotolyl indazol[3,2-b]quinazolin-7(5H)-one

[0064]

[0065] 50ml solvent acetic acid is added in the reaction vessel, then add 10mmol (II) compound, 1.5mmol Pd(OAc) 2 , 50mmol of silver acetate, under the stirring of the stirring bar, heat up to 100 ℃ and seal the reaction for 30 hours.

[0066] After the reaction finished, the reaction mixture was cooled to room temperature, transferred to a separatory funnel, added ethyl acetate that was 3-5 times the volume of the mixture, and then added a 20% aqueous sodium hydroxide solution to adjust the pH value of the system to Alkaline, liquid separation, the organic layer was washed 1-3 times with saturated brine, and then rotatively evaporated, and the residue was passed through a 300-400 mesh silica gel column with ethyl acetate / petroleum ether as the eluent, in which ethyl acetate and petroleum The volume ratio of ether was 1:15, and the target product formula (I) compound 5-p-trifluorophenylindaz...

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Abstract

The invention relates to a method for synthesizing quinazolino indazole derivatives under acidic condition, which comprises the following steps: under existence of a catalyst and an oxidizing agent, an intramolecular dehydrogenation coupling reaction of 2-aryl-3-aryl amino quinazolinone derivatives is produced in an acidic organic solvent so as to obtain the quinazolino indazole derivatives with diversified structures. The method is characterized in that under the synergistic effect of the catalyst, the oxidizing agent and the acidic organic solvent, a reaction for efficiently synthesizing the quinazolino indazole derivatives by a one-pot method is achieved, and the method has the advantages of high efficiency, environmental friendliness, high yield and purity and the like, and has good research value and application prospect.

Description

technical field [0001] The invention provides a method for synthesizing quinazolinone-indazole derivatives, more specifically, a method for synthesizing quinazolinone-indazole derivatives under acidic conditions, which belongs to the field of organic chemical synthesis. Background technique [0002] As a new class of polycyclic nitrogen-containing heterocyclic compounds, quinazolinones can be used as structural building blocks of active drugs, pesticide compounds, etc., and play an important role in the field of organic chemistry. , chemical industry, etc. have broad application prospects. For example, many drugs such as the antihypertensive drug prazosin and the diuretic drug mebazolone belong to the class of quinazolinones. And in agricultural methods, it can be used as fungicide, herbicide, etc. For example, the high-efficiency acaricide Fenazaquin has been introduced to the market as an agricultural fungicide, and the modified quinazolinone heterocyclic skeleton can be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 吴华悦杨渭光陈久喜刘妙昌黄小波高文霞
Owner WENZHOU UNIVERSITY
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