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Triketone-based compound preparation method

A technology for compounds and triketones, which is applied in the field of preparing triketone compounds, can solve the problems of hindered synthesis of homogentisic acid, complicated process routes and high commercial cost of compounds, and achieves the effects of low cost and high purity

Active Publication Date: 2018-06-15
WEIFANG CYNDA CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The mechanism of action of 4-HPPD herbicide is to inhibit the process of converting p-hydroxyphenylpyruvate into homogentisic acid in plants. Homogentisic acid can be further biocatalyzed into plastoquinone and tocopherol in plants, and plastoquinone And tocopherol is a necessary substance for electron chain transfer in plant photosynthesis. If 4-HPPD is inhibited in plants, the synthesis of homogentisic acid will be blocked, which will affect the photosynthetic electron chain transfer in plants, resulting in albinism symptoms in plants and die
However, the commercial cost of the compound of the structure shown in the formula (II) in the method of the prior art is high; when self-synthesizing, there is the shortcoming that the process route is complicated and the yield is very low

Method used

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Examples

Experimental program
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preparation example 1

[0094] Preparation example 1: using figure 1 The compound shown in the route synthetic formula (5) shown, wherein, R 3 for H, R 1 and R 2 for methyl

[0095] 1. Add water (500mL) into a 1000mL four-necked flask, start stirring, cool the system to 5°C with ice-salt water, then slowly add potassium hydroxide (553mmol) into a 100mL four-necked flask, and the addition is complete Finally, remove the icy brine, and slowly add 2,4-dimethylnitrobenzene (3311 mmol) dropwise. After the dropwise addition, the reaction system is heated to 90°C. After the reaction system rose to 90°C, potassium permanganate (1659mmol) was added to the four-necked flask in batches within 0.5h. After the addition was complete, the reaction system was kept at 90°C for 3h, and the reaction was followed by HPLC. After the reaction is completed, filter while hot and wash the filter cake with 500 mL of hot water (70° C.). The filtrate was cooled to 5° C., and concentrated hydrochloric acid (36% by weight, 1...

preparation example 2

[0100] Preparation example 2: the compound shown in preparation formula (2), and R 1 and R 2 is methyl, R 3 for H

[0101] 1. Add carbon tetrachloride (100mL) and methyl 2-aminobenzoate (149mmol) into a 250mL four-necked flask, start stirring, and start to add bromine (156.45mmol) dropwise. After the dropwise addition, take a sample by HPLC Track reactions. After the reaction was completed, the reaction solution was filtered, the filter cake was rinsed with 200 mL of isopropyl ether, and dried to obtain a yellow solid with a purity of 96.5% and a yield of 90%.

[0102] 2. Add pyridine (250mL) and the product obtained in step 1 (144mmol) into a 500mL four-neck flask, start stirring, then add 2,6-dimethylphenylisocyanate (179mmol), after the addition is complete, the reaction system Raise the temperature to 100°C and keep it overnight, and track the reaction by HPLC. After the reaction was completed, the reaction solution was poured into 1 L of water while it was hot, stirr...

preparation example 3

[0103] Preparation example 3: the compound shown in preparation formula (4), and R 1 and R 2 is methyl, R 3 for H

[0104] Add DMF (300mL) and methyl 2-amino-5-bromobenzoate (130.4mmol) into a 1000mL single-necked bottle, start stirring, and then add cuprous cyanide (2260.8mmol). After the addition was complete, the reaction system was heated to reflux and kept overnight, and the reaction was tracked by HPLC. After the reaction is completed, lower the reaction solution to 25°C, then add 500 mL of water to the reaction solution and stir for 30 minutes, then add 300 mL of ethyl acetate to it, filter after the stirring is completed, and let the filtrate stand for stratification. The aqueous phase was extracted three times with 600 mL of ethyl acetate, and the organic phase was dried with anhydrous sodium sulfate and precipitated to obtain a white solid with a purity of 95.6% and a yield of 90%.

[0105] 2. Add pyridine (167mL), the product obtained in step 1 (113.6mmol) into ...

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Abstract

The invention relates to the field of preparation of pesticides, and discloses a triketone-based compound preparation method, wherein the triketone-based compound has a structure represented by a formula (1). The method comprises that 1) a compound represented by a formula (2), 1,3-cyclohexanedione and CO are subjected to a reaction in the presence of a first catalyst under an alkali condition toobtain a product represented by a formula (3); and 2) the product represented by the formula (3) contacts a second catalyst and an alkali substance under a rearrangement reaction condition to obtain the triketone-based compound represented by the formula (1). According to the present invention, with the method, the triketone-based compound can be obtained in the low-cost and high-yield manner; andthe purity of the triketone-based compound obtained through the method is high. The formulas (1), (2) and (3) are defined in the specification.

Description

technical field [0001] The invention relates to the field of pesticide preparation, in particular to a method for preparing triketone compounds. Background technique [0002] 4-Hydroxyphenylpyruvate dioxygenase (4-HPPD) is a new herbicide target discovered in the 1980s, and it widely exists in various aerobic organisms. The enzyme is a ferrous-containing α-ketoacid-dependent dioxidase that catalyzes the conversion of p-hydroxyphenylpyruvate to homogentisate. The mechanism of action of 4-HPPD herbicide is to inhibit the process of converting p-hydroxyphenylpyruvate into homogentisic acid in plants. Homogentisic acid can be further biocatalyzed into plastoquinone and tocopherol in plants, and plastoquinone And tocopherol is a necessary substance for electron chain transfer in plant photosynthesis. If 4-HPPD is inhibited in plants, the synthesis of homogentisic acid will be blocked, which will affect the photosynthetic electron chain transfer in plants, resulting in albinism s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/96
CPCC07D239/96
Inventor 王现全杨光富姜雪峰李凯宋萍
Owner WEIFANG CYNDA CHEM
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