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Biphenyl heterocyclic compound as well as synthesis method and application thereof

A technology for a heterocyclic compound and a synthesis method, which is applied in the synthesis and antifouling fields of biphenyl heterocyclic compounds, can solve the problems of aggravating the corrosion and damage of marine engineering materials, endangering the marine ecological environment, reducing the performance of marine facilities, etc., so as to avoid artificial The effect of synthesis, price advantage, simple structure

Active Publication Date: 2022-01-11
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(3) Accelerate the corrosion damage of marine engineering materials and reduce the performance of marine facilities
At present, the most effective anti-fouling method is to paint anti-fouling coatings containing toxic anti-fouling agents such as organotin. However, this anti-fouling coating seriously endangers the marine ecological environment while preventing pollution.

Method used

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  • Biphenyl heterocyclic compound as well as synthesis method and application thereof
  • Biphenyl heterocyclic compound as well as synthesis method and application thereof
  • Biphenyl heterocyclic compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The synthesis process, steps are as follows:

[0031] (1) Add 20mL of dichloroethane and 5.2g (0.03mol) of 2-bromo-4-fluoroaniline into a 250mL three-neck flask, add 3.1g (0.03mol) of acetic anhydride dropwise at room temperature, and complete the dropwise addition in 20 minutes. Sampling was carried out to obtain intermediate 1 (acetanilide) with a yield of 99%.

[0032] (2) At room temperature, the compound 2-bromo-4-fluoroacetanilide (3.7g, 16mmol) and 3,4-dichlorobromobenzene (3.6g, 16mmol) were dissolved in THF (50mL), electromagnetically stirred, and then Magnesium chloride reagent (4.9 g, 24 mmol) was added dropwise and reacted at 50° C. for 2 h. In another three-necked flask, FeBr will be added 2 (1.16g, 10mmol) in THF (50mL), after stirring for 30min, the above-mentioned mixture was added to the solution, and after continuing to react for 20min, the oxidant BQ (2.16g, 20mmol) was added and reacted at room temperature for 30min, and the reaction solution was...

Embodiment 2-20

[0040] Table 1 Physicochemical properties of antifouling compounds

[0041]

Embodiment 2

[0043] Identification

[0044] Compound 2.1 H-NMR (400MHz,) δ8.30–8.15 (m, 2H), 8.39–8.09 (m, 2H), 7.93 (d, J=8.1Hz, 1H), 8.02–7.76 (m, 2H), 7.87 ( dd,J=5.9,3.2Hz,1H),8.79–6.57(m,16H),7.50(ddd,J=25.6,11.8,5.5Hz,8H),7.50(ddd,J=25.6,11.8,5.5Hz, 7H), 7.22–7.13(m,1H), 7.38–7.14(m,3H), 7.14–6.94(m,1H), 7.07–6.99(m,1H).

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PUM

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Abstract

The invention relates to a biphenyl heterocyclic compound as well as a synthesis method and application thereof. The general formula of the biphenyl heterocyclic compound is described in the specifications. The synthesis process of the biphenyl heterocyclic compound is simple; a cheap and low-toxicity magnesium reagent is adopted as a catalyst to replace precious metals such as palladium and platinum which are high in toxicity and high in price; the product purity is high; and the compound has bactericidal activity, has very high bactericidal activity on staphylococcus aureus and escherichia coli, and has a bright antifouling application prospect.

Description

technical field [0001] The invention belongs to the technical field of marine pollution prevention and control, and in particular relates to the synthesis and antifouling technology of biphenyl heterocyclic compounds. Background technique [0002] Marine biofouling refers to the undesirable deposition of harmful micro or large organisms in seawater on the surface of objects. It is a biological hazard that humans have encountered since they began to engage in marine activities. The hazards of marine biofouling are mainly manifested in the following aspects: (1 ) increases the navigation resistance of the ship, resulting in an increase in power consumption. According to statistics, the additional consumption caused by biofouling reaches 60 billion U.S. dollars every year, while the annual consumption for cleaning and preventing marine biofouling reaches 5.7 billion U.S. dollars. (2) Increased fuel combustion due to biofouling is expected to increase CO by 38% to 72% by 2020 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/81C07D241/24C07C235/56C07C233/66C07C235/84C07D213/82A01N43/40A01N43/60A01N37/40A01N37/42A01N37/22A01P1/00
CPCC07D213/81C07D241/24C07C235/56C07C233/66C07C235/84C07D213/82A01N43/40A01N43/60A01N37/40A01N37/42A01N37/22
Inventor 郑绍军姜乔榉武文斌谈祎杨程韩珂朱瑞陈立庄李照磊宋恒蒋春辉
Owner JIANGSU UNIV OF SCI & TECH
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