A kind of synthetic technique of 1,4 benzoxazinone compound

A technology of benzoxazinones and compounds, which is applied in the direction of organic chemistry, can solve the problems of complex synthesis methods of intermediates, high purity requirements of raw materials, air and light sensitivity, etc., so as to avoid instability and unsafety and low price , the effect of simple reaction conditions

Active Publication Date: 2020-12-01
新昌县勤勉生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the prior art method, the synthesis method of the intermediate involved is complex, and in the method of amide cyclization, many complicated factors will appear when large-scale production, for example, the nitro-substituted intermediate compound is a potential explosive intermediate The amino-substituted intermediate compound is an unstable substance, sensitive to air and light, and easily leads to side reactions
[0010] The existing technology also adopts microwave synthesis process. Although the process itself is relatively simple, microwave heating has very strict requirements on equipment and temperature control devices, and has high requirements on the purity of raw materials, so the application in industrial scale is limited.

Method used

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  • A kind of synthetic technique of 1,4 benzoxazinone compound
  • A kind of synthetic technique of 1,4 benzoxazinone compound
  • A kind of synthetic technique of 1,4 benzoxazinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of 6-amino-1,4-benzoxazin-3-(4H)-one

[0026]

[0027] Add appropriate amount of DMF and dichloromethane mixed solvent (30ml) in the reactor, add 3,4-dichloroaniline (10mmol) under stirring, glycolamide (10mmol), copper acetylacetonate catalyst (0.5mmol), N,N '-Dimethylethylenediamine (0.5mmol), NaOH (1mmol), then heated the reactant to 50°C for reaction, reacted for 5 hours, after TLC detection, the reaction was completed, the reaction mixture was poured into saturated saline, stirred rapidly , a large amount of solid precipitated out,

Embodiment 2

[0028] Example 2: Preparation of 6-methyl-1,4-benzoxazin-3(4H)-one

[0029]

[0030] Add appropriate amount of DMF and methylene chloride (30ml) in the reactor, add 4-methyl-1,2-dichlorobenzene (12mmol) under stirring, glycolamide (13mmol), copper acetylacetonate catalyst (0.5mmol), N, N'-dimethylethylenediamine (0.5mmol), KOH (1mmol), then heated the reactant to 60°C for reaction, reacted for 5 hours, and after the reaction was detected by TLC, the reaction mixture was poured into saturated saline , stirred rapidly, a large amount of solids precipitated, filtered with suction and dried to obtain a white solid, yield: 98.4%. 1 H NMR (500MHz, DMSO-d 6 / TMS int ), δ: 2.12 (s, 3H), 4.40 (s, 2H), 6.48-6.73 (m, 3H), 10.82 (s, 1H).

Embodiment 3

[0031] Example 3: Preparation of 6-methoxy-1,4-benzoxazin-3(4H)-one

[0032]

[0033] Add appropriate amount of DMF and dichloromethane (30ml) in the reactor, add 4-methoxy-1,2-dichlorobenzene (12mmol) under stirring, glycolamide (13mmol), copper acetylacetonate catalyst (0.5mmol) , N, N'-dimethylethylenediamine (0.5mmol), NaOH (1mmol), then the reactant was heated to 60°C for reaction, reacted for 5 hours, after the reaction was detected by TLC, the reaction mixture was poured into saturated salt In water, stirred rapidly, a large amount of solids precipitated, suction filtered and dried to obtain a white solid, yield: 99.5%. 1 H-NMR (CDCl 3 -d) δ: 3.75 (s, 3H); 4.55 (s, 2H); 6.40 (d, 1H); 6.50 (dd, 1H); 6.89 (d, 1H); 8.85 (bs, 1H).

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Abstract

The invention relates to a synthesis technology of benzoxazinone compounds represented by formula I. The technology is characterized in that a dichlorobenzene derivative represented by formula II reacts with ethanolamide represented by formula III in the presence of a catalyst and an inorganic alkali to obtain the compound of formula I. R in the formula I and the formula II is selected from hydrogen, an amino group, a nitro group, a C1-6 alkyl group, a C1-6 alkoxy group and a hydroxyl group. The technology is a one-pot reaction method, realizes one-step direct cyclization, and has the advantages of simple reaction conditions, convenience in treatment, safe and highly-effective process, and high yield.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a synthesis process of a 1,4-benzoxazinone compound. Background technique [0002] Chemical pesticides are increasingly polluting the environment and food, and the resistance of pathogens to existing varieties has also prompted people to continuously study how to improve the resistance of plants to prevent and control plant diseases and insect pests. An important defense method for plants is through their own biological Metabolites to fight against pests and diseases, and benzoxazinone derivatives are important secondary metabolites of grass plants, and are very important natural pesticides, with good antibacterial, antimicrobial, antifeedant and low biological toxicity. Scientists have conducted a lot of research on benzoxazinone compounds for the preparation of new herbicides, screening effective antibacterial benzoxazinone compounds so as to increase the content of such compou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/36
CPCC07D265/36
Inventor 邹明珠
Owner 新昌县勤勉生物医药科技有限公司
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