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4-Amino quinazoline compound as well as preparation method and application thereof

A technology for aminoquinazolines and compounds, which is applied in the field of quinazoline compounds substituted by aromatic ring methylene groups and their preparation, and can solve the problems of agricultural production loss, insufficient activity of commercialized antibacterial agents, and serious harm

Inactive Publication Date: 2019-05-07
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In recent years, plant bacterial diseases (such as rice bacterial blight and citrus canker, etc.) have occurred and become popular in my country on a large scale, and the main economic crop diseases have shown high frequency of occurrence, severe damage, wide occurrence range, and great difficulty in prevention and control. and other characteristics, which often cause great losses to my country's national economy, especially agricultural production, and the activity of existing commercial antibacterial agents (such as eclopyrazole, thiabylcopper, ketal, etc.) is not efficient enough, and it is urgent to find highly effective anti-plant disease bacteria active compounds, and on this basis, create new green pesticides with independent intellectual property rights, providing candidate drugs for the prevention and control of bacterial diseases of crops

Method used

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  • 4-Amino quinazoline compound as well as preparation method and application thereof
  • 4-Amino quinazoline compound as well as preparation method and application thereof
  • 4-Amino quinazoline compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the preparation of 5-chloroquinazolin-4 (3H)-one

[0061] Put 6-chloro-2-aminobenzoic acid (87.0mmol) in a 100mL round-bottomed flask, add 30mL formamide to it and stir, heat to 145°C for 5h, then stop the reaction, cool to room temperature, filter with suction, wash with water to obtain off-white Solid, the yield after drying is 76.0%.

Embodiment 2

[0062] Embodiment 2: the preparation of 4,5-dichloroquinazole

[0063] Put 5-chloroquinazolin-4(3H)-one (11.0mmol) in a 100mL round bottom flask, add 20mL of toluene to it and stir to dissolve, then add 5 equivalents of POCl to the system 3 and 2 equivalents of triethylamine, heated to reflux at 120°C, reacted for 5 hours, stopped the reaction, dissolved the solid with 100mL DCM, adjusted the pH to 6-7 with ammonia water, washed with water (30mL*3), and purified by column chromatography ( PE:EA=10:1), a white solid was obtained with a yield of 54.4%.

Embodiment 3

[0064] Embodiment 3: Preparation of 5-chloro-N-(furan-2-methylene)quinazolin-4-amine

[0065] Add 5-chloroquinazoline (5mmol) into a 50mL round bottom flask, add 20mL of dry isopropanol and stir to dissolve, then add 1.5 equivalents of triethylamine and 1.2 equivalents of 2-furylmethylamine, react at 80°C for 1 hour, then stop the reaction , precipitation, and column chromatography (eluent PE:EA=15:1) to obtain a white solid with a yield of 76.9%.

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PUM

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Abstract

The invention relates to a 4-amino quinazoline compound as well as a preparation method and application thereof. The compound has a general formula I) as shown in the specification, a quinazoline compound is taken as a basis, an aromatic ring methylene is introduced into the system for synthesizing a series of aromatic ring-containing methylene substituted 4-amino quinazoline compounds, the compound has a good inhibiting effect on pathogenic bacteria of plants, and has a good inhibiting effect on pathogenic bacteria such as xanthomonas oryzae, Xanthomonas citri and the like.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a quinazoline compound substituted with an aromatic ring methylene group and a preparation method and application thereof. Background technique [0002] In recent years, plant bacterial diseases (such as rice bacterial blight and citrus canker, etc.) have occurred and become popular in my country on a large scale, and the main economic crop diseases have shown high frequency of occurrence, severe damage, wide occurrence range, and great difficulty in prevention and control. and other characteristics, which often cause great losses to my country's national economy, especially agricultural production, and the activity of existing commercial antibacterial agents (such as eclopyrazole, thiabylcopper, ketal, etc.) is not efficient enough, and it is urgent to find highly effective anti-plant disease bacteria active compounds, and on this basis, create new green pesticides wit...

Claims

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Application Information

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IPC IPC(8): C07D239/94C07D405/12C07D401/12C07D409/12A01N43/54A01P1/00A01P3/00
Inventor 杨松龙青素王培义赵永亮吴元元薛伟
Owner GUIZHOU UNIV
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