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4-N-substituted-5-chloroquinazoline compound and preparation method and application thereof

A technology of chloroquinazoline and compounds, applied in the field of preparation of 4-N-substituted-5-chloroquinazoline compounds

Active Publication Date: 2014-08-13
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Agents for the prevention and treatment of plant bacterial diseases include organic phosphorus, organic nitrogen, heterocyclic compounds such as phenylamides and thiazoles, and antibiotics, but so far, there is no chemical pesticide on the market that can completely and effectively control the occurrence of plant bacterial diseases. Therefore, , the synthesis of low-toxic new anti-plant pathogens has become a key problem that needs to be solved urgently

Method used

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  • 4-N-substituted-5-chloroquinazoline compound and preparation method and application thereof
  • 4-N-substituted-5-chloroquinazoline compound and preparation method and application thereof
  • 4-N-substituted-5-chloroquinazoline compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0089] Example 1, 5-chloro- N -(3-fluorophenethyl)-4-aminoquinazoline (the number of the compound is I 2 )Synthesis

[0090] (1) Synthesis of 5-chloroquinazolin-4(3H)-one

[0091] Into a 25 mL three-neck flask, put 0.86 g (0.005 mol) of 2-amino-6-chlorobenzoic acid, add 3 mL (0.020 mol) of formamide, mix and heat to reflux (140°C) for 6 h, then add 10 mL of water, stir until the temperature is 60°C, then add an appropriate amount of water, cool to room temperature, and filter with suction to obtain 0.61 g of light brown powder, with a yield of 67.8%, m.p. 212 ~ 214°C (literature value 210°C);

[0092] (2) Synthesis of 4,5-dichloroquinazoline

[0093] Into a 50 mL three-neck flask, put 1.00 g (5.42 mmol) of 5-chloroquinazolin-4(3H)-one, and add 13.0 mL POCl 3 and 6 mL of triethylamine, mixed and heated to reflux for 8 h, and distilled under reduced pressure to remove excess POCl 3 , cooled, and added 30 mL CH 2 Cl 2 Dissolve the reaction product, then put the CH 2 Cl...

example 2

[0096] Example two 5-chloro- N -(3,4-dimethoxyphenethyl)-4-aminoquinazoline (the compound number is I 3 )Synthesis

[0097] (1) Synthesis of 5-chloroquinazolin-4(3H)-one

[0098] As in Example 1 (1) synthesis steps and process conditions, the difference is that the molar ratio of 2-amino-6-chlorobenzoic acid to formamide is 1:3.5, the reaction temperature is 120°C, the reaction time is 5h, and the amount of water added per 0.86g 2 - Add 20 mL of water to amino-6-chlorobenzoic acid, add in two times;

[0099] (2) Synthesis of 4,5-dichloroquinazoline

[0100] As in embodiment one (2) synthesis steps and processing conditions, the difference is that 5-chloroquinazoline-4( 3H )-ketone, phosphorus oxychloride and triethylamine mol ratio is 1:12:5.5, and reaction time 9h, 5-chloroquinazoline-4( 3H )-ketone and the mol ratio of dichloromethane is 1:26.5, every 1.00g of 5-chloroquinazoline-4( 3H )-ketone plus 1 mol / L glacial hydrochloric acid 32mL, add in two times;

[0101] (...

example 3

[0103] Example three 5-chloro- N -(2-fluorophenethyl)-4-aminoquinazoline (the compound number is I 4 )Synthesis

[0104] (1) Synthesis of 5-chloroquinazolin-4(3H)-one

[0105] As in Example 1 (1) synthesis steps and process conditions, the difference is that the molar ratio of 2-amino-6-chlorobenzoic acid to formamide is 1:4.5, the reaction temperature is 150°C, the reaction time is 7h, and the amount of water added per 0.86g 2 - Add 24mL of water to amino-6-chlorobenzoic acid, add in two times;

[0106] (2) Synthesis of 4,5-dichloroquinazoline

[0107] As in embodiment one (2) synthesis steps and processing conditions, the difference is that 5-chloroquinazoline-4( 3H )-ketone, phosphorus oxychloride and triethylamine mol ratio is 1:14:6.5, and reaction time 7h, 5-chloroquinazoline-4( 3H )-ketone and the mol ratio of dichloromethane are 1:27.5, every 1.00g of 5-chloroquinazoline-4( 3H )-ketone plus 1 mol / L glacial hydrochloric acid 34mL, add in two times;

[0108] (3) ...

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Abstract

The invention discloses a preparation method and biological activity of a compound with a function of resisting plant germs, 4-N-substituted-5-chloroquinazoline compound which is a compound represented by the general formulas (I) and (II) and a preparation method thereof. According to the invention, the 4-N-substituted-5-chloroquinazoline derivative is synthesized via three or five steps by adopting 2-amino-6-chlorobenzoic acid, formamide, phosphoryl chloride, concentrated hydrochloric acid, N-Boc piperazine and substituted benzyl chloride or benzyl bromine as raw materials and adopting sodium hydride, triethylamine and potassium carbonate as catalysts. The compounds I2, I4, I8 and II5 disclosed by the invention have relatively good inhibiting effects on plant fungi, and the compounds II1, II7, II10, II11, II16 and II17 show relatively high bacteriostatic activity on plant bacteria.

Description

technical field [0001] The present invention relates to the field of organic synthesis and pesticide technology, specifically a kind of 4- N -Preparation method and application of substituted-5-chloroquinazoline compounds. Background technique [0002] In the development of pesticides in recent years, quinazoline (ketone) compounds have attracted much attention because of their broad-spectrum biological activities and variable structure types. Many compounds containing quinoline ring structures have shown wide application and development prospects. Such as bactericidal, insecticidal, antiviral, anti-inflammatory, anti-tumor, anti-hypertensive, anti-tuberculosis, anti-malarial, etc., some quinazoline compounds have been successfully developed into commercialized drugs, such as the fungicide fluoroquinazole, The mite agent fenazaquin and the anticancer drug Iressa, etc. For a long time, people have done a lot of research on the control of plant pathogenic fungus diseases, ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/94A01N43/54A01N43/60A01P3/00A01P1/00
CPCA01N43/54A01N43/60C07D239/94
Inventor 杨松向红梅薛伟丁永正张东阳施利尹娟贺鸣
Owner GUIZHOU UNIV
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