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2, 3, 4, 7-tetrahydro-1h-nitrogen azepine compound and preparation method and application thereof

A compound, azapine technology, applied in the field of organic synthesis, can solve problems such as rare synthetic methods

Inactive Publication Date: 2012-06-27
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these 2,3,4,7-tetrahydro-1H-azepine compounds and analogues play an important role in the research of biologically active molecules, relatively successful synthetic methods are relatively rare. Therefore, the development of simple and practical Efficient synthetic methods to synthesize these compounds and study their biological activities have been paid much attention

Method used

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  • 2, 3, 4, 7-tetrahydro-1h-nitrogen azepine compound and preparation method and application thereof
  • 2, 3, 4, 7-tetrahydro-1h-nitrogen azepine compound and preparation method and application thereof
  • 2, 3, 4, 7-tetrahydro-1h-nitrogen azepine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1, 1-p-nitrobenzenesulfonyl-3-phenyl-2,3,4,7-tetrahydro-1H-azepine-4,5-dicarboxylic acid diethyl represented by formula (IV) Synthesis of esters

[0028]

[0029] Compound 1-p-nitrobenzenesulfonyl-2-phenylaziridine (0.125mmol), 5mL dichloromethane and 0.0297g formula (II) shown in 0.0381g formula (II) 2-vinylsuccinate Diethyl diethyl ester (0.150mmol) was put into a 15mL Shrek tube dried in an oven, and the phosphine catalyst propyldiphenylphosphine (0.125mmol) was added, and the cycloaddition reaction was carried out with stirring. In this reaction system, 1-p The molar ratio of nitrobenzenesulfonyl-2-phenylaziridine to 2-vinylsuccinic acid diethyl ester is 1:1.2, and ethyldiphenylphosphine accounts for 1-p-nitrobenzenesulfonyl-2-benzene The molar percentage of aziridine is 100%, stirred at 25 DEG C for 48 hours, passed through the column after concentrating the reaction solution with a rotary evaporator (ethyl acetate: petroleum ether=1: 8, v / v), and obtai...

Embodiment 2

[0031] Example 2, 1-p-nitrobenzenesulfonyl-3-o-bromophenyl-2,3,4,7-tetrahydro-1H-azepine-4,5-dicarboxylic acid represented by formula (V) Synthesis of Diethyl Ester

[0032]

[0033]Compound 1-p-nitrobenzenesulfonyl-2-o-bromophenylaziridine (0.125mmol) shown in 0.0481g formula (I), 5mL dichloromethane and 0.0495g compound 2-ethylene shown in formula (II) Diethyl succinate (0.250mmol) was put into a 15mL Shrek tube dried in an oven, the phosphine catalyst ethyldiphenylphosphine (0.0625mmol) was added, and the cycloaddition reaction was carried out with stirring. In the reaction system, 1 - The molar ratio of p-nitrobenzenesulfonyl-2-o-bromophenylaziridine to 2-vinylsuccinic acid diethyl ester is 1:2, and ethyldiphenylphosphine accounts for 1-p-nitrobenzenesulfonyl The molar percentage of -2-o-bromophenylaziridine is 50%, stirred at 30°C for 72 hours, concentrated the reaction solution with a rotary evaporator, and passed the column (ethyl acetate:petroleum ether=1:8, v / v)...

Embodiment 3

[0035] Example 3, 1-p-nitrobenzenesulfonyl-3-m-methylphenyl-2,3,4,7-tetrahydro-1H-azepine-4,5-dicarboxylic acid represented by formula (VI) Synthesis of Diethyl Acetate

[0036]

[0037] Compound 1-p-nitrobenzenesulfonyl-2-m-tolyl aziridine (0.125mmol) shown in 0.0399g formula (I), 5mL dichloromethane and 0.0742g compound 2-vinyl shown in formula (II) Diethyl succinate (0.375mmol) was put into a 15mL Shrek tube dried in an oven, the phosphine catalyst butyldiphenylphosphine (0.025mmol) was added, and the cycloaddition reaction was carried out with stirring. In the reaction system, 1- The molar ratio of p-nitrobenzenesulfonyl-2-p-tolyl aziridine to 2-vinylsuccinic acid diethyl ester is 1:3, and butyldiphenylphosphine accounts for 1-p-nitrobenzenesulfonyl-2 -The molar percentage of p-tolyl aziridine is 20%, stirred at 40°C for 48 hours, concentrated the reaction solution with a rotary evaporator and passed it through the column (ethyl acetate:petroleum ether=1:8, v / v), 18.2...

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Abstract

The invention discloses a 2, 3, 4, 7-tetrahydro-1H-nitrogen azepine compound represented by formula (III) and a preparation method and application thereof. The preparation method comprises the following step: the 2, 3, 4, 7-tetrahydro-1H-nitrogen azepine compound is prepared by cycloaddition reaction of a compound represented by formula (I) and a compound represented by formula (II) in the presence of a phosphine catalyst. The application of the 2, 3, 4, 7-tetrahydro-1H-nitrogen azepine compound represented by the formula (III) is further provided in the preparation process of herbicide whichcan prevent and remove crabgrass and rape. The method adopts a cycloaddition mode to perform the reaction which belongs to atom economical reaction. Organic phosphine is adopted to serve as the catalyst and a transition metal catalyst is not used so that no heavy metal residual pollutant exists. The prepared 2, 3, 4, 7-tetrahydro-1H-nitrogen azepine compound is a novel compound and has a certain herbicidal activity.

Description

technical field [0001] The invention relates to a 2,3,4,7-tetrahydro-1H-azepine compound and a preparation method and application thereof, belonging to the field of organic synthesis. Background technique [0002] 2,3,4,7-tetrahydro-1H-azepine compounds and their analogues have diverse biological activities and are of great research value in the fields of medicine and pesticides. In the existing studies, these compounds generally show good herbicidal activity, so they have received a lot of attention. Although these 2,3,4,7-tetrahydro-1H-azepine compounds and analogs play an important role in the research of biologically active molecules, relatively successful synthetic methods are relatively rare. Therefore, the development of simple and practical Efficient synthetic methods to synthesize these compounds and study their biological activities have been paid much attention. [0003] Nucleophilic organophosphine-catalyzed intermolecular cycloaddition reactions are one of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/06A01N43/46A01P13/00
Inventor 郭红超王敏刘洪蕾荆呈峰那日松钟江春
Owner CHINA AGRI UNIV
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