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Method for synthesizing quinazolino indazole derivatives

A synthesis method and quinazolinone technology are applied in the field of organic chemical synthesis and can solve problems such as environmental pollution and damage

Inactive Publication Date: 2014-03-26
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As we all know, the use of halides has caused great damage to environmental pollution

Method used

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  • Method for synthesizing quinazolino indazole derivatives
  • Method for synthesizing quinazolino indazole derivatives
  • Method for synthesizing quinazolino indazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0058] Preparation 1: 2-Phenyl-3-(phenylamino)quinazolin-4(3H)-one

[0059] (1). Add 10mmol anthranilic acid and 20mmol sodium carbonate to a 100mL round bottom flask, then add 20mL THF, stir in an ice-water bath, add 25mmol benzoyl chloride, stir for 15 minutes, then warm to room temperature And continue to stir and react overnight, after the reaction is finished, add water to separate out the solid, filter, and the solid is rinsed with 50% methanol aqueous solution with a mass percentage concentration, and dried to obtain the product (formula (III) compound), the yield is 60%, and its melting point is 104-105°C. Its reaction formula is as follows:

[0060]

[0061] (2). Take 2mmol of the compound of formula (III) obtained in the previous step and 20mL of acetic acid into a 100mL round-bottomed flask, then add 2.5mmol of phenylhydrazine, reflux at 160°C overnight, add 30mL of water after cooling, and let the solution settle until the solution is clear. The solution was p...

preparation example 2

[0066] Preparation 2: 2-Phenyl-3-(p-tolylamino)quinazolin-4(3H)-one

[0067] Take 2mmol of the compound of formula (III) obtained in Preparation Example 1 step (1) and 15mL of acetic acid into a 100mL round-bottomed flask, then add 1.5mmol of p-methylphenylhydrazine, reflux at 140°C overnight, cool and add 25mL of water, and let it stand for precipitation To the solution clarification, the solution is poured out, and the precipitate is added with ethanol for recrystallization, filtered, rinsed with ethanol, and dried to obtain the product 2-phenyl-3-(p-tolylamino)quinazolin-4(3H)-one ( Formula (II) compound), yield 60%. Its reaction formula is as follows:

[0068]

[0069] Melting point: 181-182°C;

[0070] NMR: 1 HNMR (500Mz, DMSO-d 6 )δ8.94(s,1H),8.14(d,J=8.0Hz,1H),7.93-7.90(m,1H),7.80(d,J=8.0Hz,1H),7.75-7.73(m,2H ),7.60-7.57(m,1H),7.46-7.39(m,3H),6.92(d,J=8.5Hz,2H),6.49(d,J=8.5Hz,2H),2.14(s,3H) .

[0071] 13 CNMR (125Mz, DMSO-d 6 )δ 160.6, 157.5, 146.8, 144.7, 134...

preparation example 3

[0072] Preparation 3: 2-Phenyl-3-(p-trifluoromethylanilino)quinazolin-4(3H)-one

[0073] Except that p-methylphenylhydrazine was replaced by p-trifluoromethylphenylhydrazine, this preparation example 3 was implemented in the same manner as preparation example 2, and the product 2-phenyl-3-(p- Trifluoromethylanilino)quinazolin-4(3H)-one (compound of formula (II)), yield 62%. Its structural formula is as follows:

[0074]

[0075] Its melting point and NMR are as follows:

[0076] Melting point: 211-212°C;

[0077] NMR: 1 HNMR (500Mz, DMSO-d 6 )δ9.64(s,1H),8.17(d,J=8.0,1.0Hz,1H),7.95-7.92(m,1H),7.82(d,J=8.0Hz,1H),7.72-7.71(m ,2H), 7.63-7.60(m,1H), 7.48-7.41(m,5H), 6.78(d,J=8.5Hz,2H).

[0078] 13 CNMR (125Mz, DMSO-d 6 )δ 160.3, 157.1, 150.2, 146.7, 135.1, 133.9, 129.9, 128.7 (2C), 127.8, 127.6 (2C), 127.3, 126.3 (2C), 123.5, 120.1, 119.8, 119.5, 112.1 (2C).

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Abstract

The invention relates to a method for synthesizing quinazolino indazole derivatives. The method comprises the following steps: using a palladium compound as a catalyst, and producing an intramolecular dehydrogenation coupling reaction of 2-aryl-3-aryl amino quinazolinone derivatives in an oxygen atmosphere in the presence of alkali and a molecular sieve so as to obtain the quinazolino indazole derivatives with diversified structures. The method overcomes the defect that a halogenated compound has to be used as a reaction substrate in the prior art under the synergistic effect of the catalyst, alkali and the molecular sieve, achieves a reaction for efficiently synthesizing the quinazolino indazole derivatives by a one-pot method, has the advantages of high efficiency, environmental friendliness, high yield and purity and the like, expands the application range of the transition metal catalytic dehydrogenation coupling reaction, enriches synthetic methods and paths of the quinazolino indazole derivatives, and has very high theoretical research and application values.

Description

technical field [0001] The invention provides a method for synthesizing quinazolinone and indazole derivatives, more specifically, provides a method for synthesizing indazolone[3,2-b]quinazolinone, which belongs to the field of organic chemical synthesis . Background technique [0002] As a very important class of nitrogen-containing heterocyclic compounds, quinazolinone derivatives are widely used in medicine, agriculture, chemical industry and other industries. At present, many quinazolinone drugs have been widely used in real life, such as antihypertensive drug prazosin, diuretic drug toluene quinazolone and so on. [0003] In addition to the application in medicine, quinazolinone derivatives also play an important role in agriculture, and can be used as fungicides, herbicides, 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 used to make...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D239/92
CPCC07D239/92C07D487/04
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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