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1,2-oxinane pyrazolidone compounds and preparation method and applications thereof

A compound, alkyl technology, applied in 1 field

Inactive Publication Date: 2012-04-11
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these 1,2-azacyclooctanopyrazolidinone compounds and their analogs play an important role in the research of biologically active molecules, relatively successful synthetic methods are still 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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  • 1,2-oxinane pyrazolidone compounds and preparation method and applications thereof
  • 1,2-oxinane pyrazolidone compounds and preparation method and applications thereof
  • 1,2-oxinane pyrazolidone compounds and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of 1,2-azacyclooctan pyrazolidinone compounds shown in embodiment 1, formulas V and VI

[0034]

[0035] 0.0218g of compound 1-(benzylidene)-3-oxodihydropyrazole ylide (0.125mmol) shown in formula I, 4mL of dichloromethane, 1mL of benzene and 0.0280g of compound 2 shown in formula II, Ethyl 3-butadienoate (0.250mmol) was put into a 15mL Shrek tube dried in an oven, and the phosphine catalyst tricyclohexylphosphine 0.025mmol was added and mixed for cycloaddition reaction. In this reaction system, 1-( The molar ratio of benzylidene)-3-oxodihydropyrazole ylide to ethyl 2,3-butadienoate is 1:2.0, and tricyclohexylphosphine accounts for 1-(benzylidene)- The molar percentage of 3-oxodihydropyrazole ylide was 20%, stirred at 0°C for 120 hours, concentrated the reaction solution with a rotary evaporator, and passed the column (ethyl acetate:petroleum ether=10:1, v / v), obtain 40.3mg product, be the mixture of compound shown in formula V and VI, yield 81%, calculat...

Embodiment 2

[0040] Synthesis of 1,2-azacyclooctan pyrazolidinone compounds shown in embodiment 2, formula (VII) and (VIII)

[0041]

[0042] Compound 1-[(4-methylphenyl)methylene]-3-oxodihydropyrazole ylide (0.125mmol) shown in 0.0235g formula I, 3mL dichloromethane, 2mL benzene and 0.0308g The compound 2,3-butadienoic acid ethyl ester (0.275mmol) shown in the formula II was put into the 15mL Shrek tube dried in an oven, and the phosphine catalyst trimethylphosphine 0.0125mmol was added and mixed to carry out the cycloaddition reaction. In the reaction system, the molar ratio of 1-[(4-methylphenyl)methylene]-3-oxodihydropyrazole ylide to 2,3-butadienoic acid ethyl ester is 1: 2.2, Trimethylphosphine accounts for 10% of the molar percentage of 1-[(4-methylphenyl)methylene]-3-oxodihydropyrazole ylide, stirred at -5°C for 130 hours, and used The reaction solution was concentrated by a rotary evaporator and passed through the column (ethyl acetate:petroleum ether=10:1, v / v) to obtain 33.0...

Embodiment 3

[0047] Synthesis of 1,2-azacyclooctanopyrazolidinone compounds shown in embodiment 3, formula (IX) and (X)

[0048]

[0049] Compound 1-[(4-nitrophenyl)methylene]-3-oxodihydropyrazole ylide (0.125mmol) shown in 0.0274g formula I, 5mL dichloromethane and 0.0336g formula II Compound 2, ethyl 3-butadienoate (0.300mmol) was put into the 15mL Shrek tube dried in an oven, and the phosphine catalyst tributylphosphine 0.00625mmol was added and mixed to carry out the cycloaddition reaction. In the reaction system , The molar ratio of 1-[(4-nitrophenyl)methylene]-3-oxodihydropyrazole ylide to 2,3-butadienoic acid ethyl ester is 1:2.4, tributyl Phosphine accounts for 5% mole percent of 1-[(4-nitrophenyl)methylene]-3-oxodihydropyrazole ylide, stirred at 25°C for 80 hours, and concentrated with a rotary evaporator The reaction solution was passed through the column (ethyl acetate:petroleum ether=10:1, v / v) to obtain 29.0 mg of product, which was a mixture of compounds represented by fo...

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Abstract

The invention discloses 1,2-oxinane pyrazolidone compounds and a preparation method and applications thereof. The 1,2-oxinane pyrazolidone compounds are shown in a formula III or a formula IV. The preparation method comprises the following steps: uniformly mixing a compound shown in a formula I and a compound shown in a formula II in a solvent and reacting in the presence of a phosphine catalyst to obtain the compounds shown in the formula III or the formula IV. The invention provides a new, simple and feasible method for synthesizing the 1,2-oxinane pyrazolidone compounds; the synthesized compounds are new compounds which are not reported in literatures; in the method disclosed by the invention, the cycloaddition reaction is adopted and the method belongs to the atom economic reaction; and the method uses organic phosphine as the catalyst rather than a transition metal catalyst, thus the product does not have heavy metal residual pollutants and has weeding effect on crabgrass and barnyard grass.

Description

technical field [0001] The invention belongs to the fields of organic synthesis and pesticide science, and relates to a 1,2-azacyclooctanopyrazolidinone compound, a preparation method and application thereof. Background technique [0002] 1,2-Azacyclooctanopyrazolidinone compounds and analogues (Formula 1) have diverse biological activities, have great research value in the fields of medicine, pesticides, etc., and have been used as herbicides, pesticides, etc. Insecticides, acetyl-CoA carboxylase inhibitors, etc. have been studied, and these compounds have received more attention from the pesticide industry because of their significant herbicidal activity. Although these 1,2-azacyclooctanopyrazolidinone compounds and their analogs play an important role in the research of biologically active molecules, relatively successful synthetic methods are still relatively rare. Therefore, the development of simple and practical efficient synthetic Methods to synthesize these compou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P7/00A01P13/00
Inventor 郭红超王敏那日松荆呈峰刘洪蕾姜辉张磊钟江春
Owner CHINA AGRI UNIV
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