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Synthetic method for cinnoline compound and agricultural biological activity thereof

A synthetic method and compound technology, applied in botany equipment and methods, chemicals for biological control, biocides, etc., can solve the problems of uneconomical, high reaction cost, high metal residue, etc., and achieve short reaction time , Low catalyst dosage, simple reaction system

Inactive Publication Date: 2019-01-18
QINGDAO AGRI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the above-mentioned preparation process, the metal catalyst used is expensive and used in a large amount, and the metal residue in the product obtained after the reaction is relatively high, so the reaction cost is high and the environment is not good, so the method currently provided is not economical , and cannot be applied to industrial production

Method used

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  • Synthetic method for cinnoline compound and agricultural biological activity thereof
  • Synthetic method for cinnoline compound and agricultural biological activity thereof
  • Synthetic method for cinnoline compound and agricultural biological activity thereof

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preparation example Construction

[0022] The embodiment of the present invention provides a kind of synthetic method of carnoline compound, comprises the following steps:

[0023] S1: Add phenylhydrazine compound and tolanyl acetylene compound respectively into the reaction container, under the action of copper sulfate and isopropanol, react for 1-2 hours under blue LED lighting at room temperature at 20-25°C;

[0024] In this step, the cinnoline compound is synthesized by using the phenylhydrazine compound and the tolan compound. Specifically, copper sulfate reacts with phenylhydrazine to generate a five-membered ring intermediate, and the tolan compound inserts the five-membered ring In the next step, another molecule of benzyne compound is inserted into the intermediate of the previous step to generate the target product. What needs to be explained here is that the reaction in this step does not need to be heated, and it can be reacted under light conditions. The amount of copper sulfate catalyst is extreme...

Embodiment 1

[0040] Add 1mmol, 2mmol, 0.003mmol copper sulfate and 2ml isopropanol to the reaction vessel respectively, and react for 1 hour under the blue 5W LED light at room temperature 20-25°C; after the reaction, add water and dichloromethane to extract , the organic layers were combined and then the organic solvent was removed to give the following C1 compound:

[0041]

[0042] Carry out nuclear magnetic spectrum analysis to above-mentioned yellow solid, data is as follows:

[0043] 1 H NMR (500MHz, CDCl 3 )δ=8.53(d, J=8.5Hz, 1H), 7.74(s, 1H), 7.61(d, J=8.2Hz, 1H), 7.58(d, J=7.0Hz, 1H), 7.43-7.31( m,6H),7.28(d,J=4.1Hz,1H),7.11(d,J=7.0Hz,2H),7.06-7.00(m,3H),6.96(t,J=7.4Hz,1H), 6.92-6.87(m, 2H), 6.85(t, J=7.6Hz, 2H), 6.56(d, J=7.3Hz, 2H), 6.23(s, 1H);

[0044] 13 C NMR (125MHz, CDCl 3 )δ=153.9, 149.0, 144.4, 141.8, 139.9, 137.1, 137.0, 133.6, 133.0, 132.1, 131.2, 130.7, 130.5, 129.7, 129.6, 129.1, 128.3, 128.1, 127.8, 120.6, 12.7 ,125.0,124.7;

[0045] After identification, t...

Embodiment 2

[0047] Add 1mmol, 2mmol, 0.003mmol copper sulfate and 2ml isopropanol to the reaction vessel respectively, and react for 1 hour under the blue 5W LED light at room temperature 20-25°C; after the reaction, add water and dichloromethane to extract , combining the organic layers and then removing the organic solvent yields the following C2 compound:

[0048]

[0049] Carry out nuclear magnetic spectrum analysis to above-mentioned yellow solid, data is as follows:

[0050] 1 H NMR (500MHz, CDCl 3 )δ=7.54(td,J=8.0,5.1Hz,1H),7.47-7.31(m,8H),7.28(s,1H),7.10(d,J=7.8Hz,2H),7.05(dd,J =5.1,1.5Hz,3H),7.00(t,J=7.4Hz,1H),6.89(t,J=7.6Hz,4H),6.58(d,J=8.1Hz,2H),6.25(s,1H );

[0051] 13 C NMR (125MHz, CDCl 3 )δ=158.6 (d, J=263.0Hz), 154.9, 144.4, 141.9, 140.3, 140.2, 139.9, 137.2, 136.7, 133.4, 132.5, 132.0, 131.4, 130.8, 130.7, 130.6, 129.8, 129.4, 128 ,127.6,127.1,127.0,126.6,126.5,121.0,113.2;

[0052] After identification, the spectral data corresponded to the structural formula,...

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Abstract

The invention provides a synthetic method for a cinnoline compound and agricultural biological activity thereof, and belongs to the field of organic synthesis. The synthetic method is simple in reaction system, has the advantages of short reaction time, low catalyst dosage and environmental friendliness, and effectively meets the requirement on green chemistry; a reaction can be finished at room temperature by only taking copper sulfate as a catalyst and taking isopropanol as a solvent under illumination condition. According to the technical scheme, the synthetic method comprises the followingsteps: adding a phenylhydrazine compound and a diphenylacetylene compound into a reaction container respectively, and reacting for 1 to 2 hours at room temperature of 20 to 25 DEG C under the light condition of a blue LED (Light-Emitting Diode) lamp under the actions of copper sulfate and isopropanol; adding water and dichloromethane for extracting at the end of the reaction, combining organic layers, and then removing an organic solvent to obtain the cinnoline compound. The cinnoline compound can be applied to the prevention and control of apple ring rot.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of cinnamon compounds and their agricultural biological activity. Background technique [0002] Cinnoline compounds have a variety of biological activities, and have achieved satisfactory multi-faceted effects in recent years, and have attracted more and more attention from chemical researchers all over the world. At present, the existing method for preparing cinnamon compounds is prepared by using phenylhydrazine compounds and tolanyl acetylene compounds to react under the action of metal catalysts (rhodium, copper) under high-temperature heating conditions. However, in the above-mentioned preparation process, the metal catalyst used is expensive and used in a large amount, and the amount of metal residues in the product obtained after the reaction is relatively high. Therefore, the reaction cost is high and the environment is not good, so the meth...

Claims

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Application Information

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IPC IPC(8): C07D237/28A01N43/58A01P3/00
CPCA01N43/58C07D237/28
Inventor 王祖利董道青杨洪迪王艳丽丁彩真李光辉李丽霞陈文静
Owner QINGDAO AGRI UNIV
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