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Preparation method of non natural isocumarin and its 3,4-dihydro derivative and use thereof

A technology of isocoumarin and its derivatives, which can be used in the fields of chemicals for biological control, biocides, and resistance to vector-borne diseases, etc., and can solve the problems of relatively few biological activity reports

Inactive Publication Date: 2006-06-14
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Many compounds in the isocoumarin derivatives disclosed in domestic and foreign patent documents have important physiological and biological activities, and coumarin compounds have been used as pesticides such as rodenticides and herbicides. There are many patents on the synthesis of coumarin derivatives, but there are relatively few reports on biological activity, especially the biological activity of pesticides. In recent years, the isocoumarin derivatives and their biological activities reported in domestic and foreign patents are shown in Table 1

Method used

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  • Preparation method of non natural isocumarin and its 3,4-dihydro derivative and use thereof
  • Preparation method of non natural isocumarin and its 3,4-dihydro derivative and use thereof
  • Preparation method of non natural isocumarin and its 3,4-dihydro derivative and use thereof

Examples

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Embodiment 1

[0045] 3, the preparation of 5-dichlorobenzoyl chloride (31'):

[0046] Add 3,5-dichlorobenzoic acid (31) (10.0g, 53.0mmol) and thionyl chloride (4.5ml, 38.0mmol) in a 500mL three-necked flask, add dropwise DMF to the mixture, and reflux for 30 minutes. When gas was generated, it was proved that the reaction was over, and the unreacted thionyl chloride was removed under reduced pressure to obtain dihalobenzoyl chloride (11 g, 50.0 mmol) (31'). The product was stored in a desiccator without purification and was used directly for the next reaction.

Embodiment 2

[0048] The preparation of 2,3-dichlorobenzoyl chloride (32'):

[0049] Add 2,3-dichlorobenzoic acid (32) (10.0g, 53.0mmol) and thionyl chloride (4.5ml, 38.0mmol) in a 500mL three-necked flask, add dropwise DMF to the mixture, and reflux for 30 minutes. When gas was generated, it was proved that the reaction was over, and the unreacted thionyl chloride was removed under reduced pressure to obtain dihalobenzoyl chloride (11 g, 50.0 mmol) (32'). The product was stored in a desiccator without purification and was used directly for the next reaction.

Embodiment 3

[0051] The preparation of 2,5-dichlorobenzoyl chloride (33'):

[0052] Add 2,5-dichlorobenzoic acid (33) (10.0g, 53.0mmol) and thionyl chloride (4.5ml, 38.0mmol) in a 500mL three-necked flask, add dropwise DMF to the mixture, and reflux for 30 minutes. When gas was generated, it was proved that the reaction was over, and the unreacted thionyl chloride was removed under reduced pressure to obtain dihalobenzoyl chloride (11 g, 50.0 mmol) (33'). The product was stored in a desiccator without purification and was used directly for the next reaction.

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PUM

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Abstract

The present invention relates to a preparation method for synthesizing non-natural isocoumarin, its 3,4-dihydroderivative and its intermediate. Said invention provides the application of isocoumarin, its 3,4-dihydroderivative and its intermediate in the fields of agricultural pesticide and medicine. Said invention also provides their structure formulae.

Description

technical field [0001] The technical scheme of the present invention relates to halogen-substituted isocoumarin derivatives and intermediates thereof, in particular to isocoumarin derivatives and intermediate ketoacid derivatives and hydroxyacid derivatives for synthesizing the products. Background technique [0002] Isocoumarin (scientific name: 1H-2-benzopyran-1-one) is the basic structure of some natural products and widely exists in nature. Its derivatives have a wide range of physiological and biological activities such as antibacterial, anti-inflammatory, anti-cancer, Inhibition of protease and herbicide, etc. and obvious anticancer activity (Li Li, Yang Jinfei, Yuan Xiangai, Synthesis Research and New Progress of Isocoumarin Compounds, Journal of Nanjing Normal University (Engineering Technology Edition), 2005, 5(2): 64 -67.). Isocoumarin and 3,4-dihydroisocoumarin are secondary metabolites of fungi, mosses, molds, bacteria, higher plants and animals. , Penicillium,...

Claims

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Application Information

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IPC IPC(8): C07D311/76A01P3/00A61P31/04A61P31/10C07C65/105C07C65/34
CPCY02A50/30
Inventor 范志金瓜勒姆﹒瓜弟尔那斯姆﹒汗山﹒拉姆
Owner NANKAI UNIV
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