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A quinazoline-containing chalcone phosphonate derivative, its preparation method and use

A technology of chalcone phosphonic acid and quinazoline, which is applied to quinazoline-containing chalcone phosphonate derivatives, the fields of preparation and use thereof, and can solve the problem of low selectivity and poor biological activity selectivity. Advanced problems, to achieve the effect of good activity

Active Publication Date: 2018-02-09
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] To sum up, the reaction selectivity of the compounds constructed in the past is low, and the selectivity of biological activity is not very high, and there is no relevant literature report on the preparation of compounds containing Synthesis and Biological Activities of Chalcone Phosphonates of Quinazolines

Method used

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  • A quinazoline-containing chalcone phosphonate derivative, its preparation method and use
  • A quinazoline-containing chalcone phosphonate derivative, its preparation method and use
  • A quinazoline-containing chalcone phosphonate derivative, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The preparation method of diethyl (3-OXO-1-phenyl-3-(4-(quinazoline-4-amino) phenyl) propyl) phosphonate (compound number is a), comprises the following steps:

[0045] (1) Preparation of quinazoline-4(3H)-one:

[0046] In a 100mL three-necked flask, add 9.30g of methyl anthranilate, 14.9g of formamide and 4mL of formic acid, mix and heat to 130-140°C, stop the reaction after 7 hours of reaction, slowly add 30mL of water, cool to room temperature, and a large amount of The solid precipitated and was filtered by suction to obtain a white solid, which was recrystallized from absolute ethanol to obtain 7.50 g of the white flocculent target product with a yield of 78.0%.

[0047] (2) The preparation of 4-chloroquinazoline:

[0048] In a 100mL three-necked flask, add 2.0g of quinazolin-4(3H)-one, 15mL of thionyl chloride, 8mL of 1,2-dichloroethane, 1mL of N,N-dimethylformamide, and start Heat to reflux, distill off the solvent under reduced pressure after 4h, add 40mL of c...

Embodiment 2

[0056] The preparation method of diethyl (1-(3-bromophenyl)-3-OXO-3-(4-(quinazoline-4-amino)phenyl)propyl) phosphonate (compound number is b) , including the following steps:

[0057] (1) Preparation of quinazoline-4(3H)-one:

[0058] As in the first (1) step of Example 1.

[0059] (2) The preparation of 4-chloroquinazoline:

[0060] As in embodiment 1 (2) step.

[0061] (3) Preparation of 1-(4-(quinazoline-2-amino)phenyl)ethanone:

[0062] As in embodiment 1 (3) step.

[0063] (4) Preparation of (E)-3-(3-bromophenyl)-1-(4-(quinazoline-4-amino)phenyl)prop-2-en-1-one:

[0064] As in the (4) step of embodiment 1, the difference is that 3-bromobenzaldehyde is used as raw material;

[0065] (5) Preparation of diethyl (1-(3-bromophenyl)-3-OXO-3-(4-(quinazoline-4-amino)phenyl)propyl) phosphonate:

[0066] As in step (5) of Example 1, the difference is that (E)-3-(3-bromophenyl)-1-(4-(quinazoline-4-amino)phenyl)prop-2-ene- 1-ketone as raw material;

Embodiment 3

[0068] The preparation method of diethyl (2-chlorophenyl)-3-OXO-3-(4-(quinazoline-4-amino) phenyl) propyl) phosphonate (compound number is c), comprises following step:

[0069](1) Preparation of quinazoline-4(3H)-one:

[0070] As in the first (1) step of Example 1.

[0071] (2) The preparation of 4-chloroquinazoline:

[0072] As in embodiment 1 (2) step.

[0073] (3) Preparation of 1-(4-(quinazoline-2-amino)phenyl)ethanone:

[0074] As in embodiment 1 (3) step.

[0075] (4) Preparation of (E)-3-(2-chlorophenyl)-1-(4-(quinazoline-4-amino)phenyl)prop-2-en-1-one:

[0076] As in the (4) step of embodiment 1, the difference is that 2-chlorobenzaldehyde is used as raw material;

[0077] (5) Preparation of diethyl (2-chlorophenyl)-3-OXO-3-(4-(quinazoline-4-amino)phenyl)propyl) phosphonate:

[0078] As in step (5) of Example 1, the difference is that (E)-3-(2-chlorophenyl)-1-(4-(quinazoline-4-amino)phenyl)prop-2-ene-1 - ketone as raw material;

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Abstract

The invention discloses a chalcone phosphonate derivative containingquinazoline and a preparation method and application of the chalcone phosphonate derivative. The structural formula (1) of the chalcone phosphonate derivative is as shownin thespecification, and in the formula, R1 is phenyl, 3-bromophenyl, 2-chlorophenyl, 4-bromophenyl, 2-fluorophenyl, 2-thienyl, 2,6-dichlorophenyl, 4-chlorophenyl, 2-furyl, 2-trifluoromethylphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-chloro-6-fluorophenyl. The chalcone phosphonate derivative is simple in synthesis route, high in yield and capable of efficiently and safely preventing and treating plant virus diseases.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a quinazoline-containing chalcone phosphonate derivative, and also to a preparation method of the quinazoline-containing chalcone phosphonate derivative, And the use of the quinazoline-containing chalcone phosphonate derivatives in inhibiting yellow scratch mosaic virus disease, tobacco mosaic virus disease, southern rice black-streaked dwarf virus disease and rice stripe leaf blight virus. Background technique [0002] Chalcones are a class of natural organic substances present in medicinal plants such as licorice and safflower. They have the characteristics of low toxicity and low residue, and because of their greater flexibility in molecular structure, they can interact with different receptors. Combined, it exhibits a wide range of biological activities, such as: antibacterial, antiviral, nematicidal, antiallergic and other biological activities. Therefore, chalcon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6512C07F9/6558A01N57/24A01P1/00A01P7/04A01P13/00
CPCA01N57/24C07F9/65128C07F9/65583C07F9/65586
Inventor 胡德禹潘建科宋宝安张国平薛伟张建李天先吴增雪
Owner GUIZHOU UNIV