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A kind of synthetic method of imidazolinone derivative

A technology of imidazolinone and synthesis method, which is applied in the field of synthesis of imidazolinone derivatives, can solve the problems of high equipment requirements, cumbersome steps, low yield, etc., and achieve the effect of meeting the synthesis requirements and having great application prospects

Active Publication Date: 2022-06-24
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above-mentioned synthesis method has the advantages of easy availability of raw materials and low price, it needs to be carried out under high temperature and high pressure conditions, which requires relatively high equipment requirements. Serious environmental pollution and other obvious deficiencies

Method used

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  • A kind of synthetic method of imidazolinone derivative
  • A kind of synthetic method of imidazolinone derivative
  • A kind of synthetic method of imidazolinone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The first embodiment of the present invention is: a method for synthesizing imidazolidinone derivatives, comprising the following steps:

[0069] 0.25 mmol of benzamidine hydrochloride, 0.375 mmol of 1,2-cyclohexanediol, 0.6 mmol of cesium carbonate, 60 mg of activated carbon-supported cobalt metal catalyst (activated carbon mass fraction of 3%) and 1 ml of pyridine, stirred and reacted at 130 ° C under air conditions for 12 hours, stopped heating and stirring, cooled to room temperature, evaporated under reduced pressure to remove the solvent, and then separated and purified by thin-layer chromatography to obtain The target product, the stationary phase of the thin-layer chromatography used is silica gel, the eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate=5:1, v / v), and the yield of the obtained product is 89% .

[0070] The hydrogen spectrogram and carbon spectrogram of the product obtained in Example 1 of the present in...

Embodiment 2

[0077] The second embodiment of the present invention is: a method for synthesizing imidazolidinone derivatives, comprising the following steps:

[0078] In a schlenk tube were added 0.25 mmol 4-methoxybenzamidine hydrochloride, 0.45 mmol 1,2 cyclohexanediol, 0.5 mmol potassium hydroxide, 45 mg alumina supported cobalt metal catalyst (trioxide). The mass fraction of aluminum oxide is 3%) and 1 ml of tert-amyl alcohol, and the reaction was stirred at 110 ° C and air for 12 hours, then heating and stirring were stopped, cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure, and then passed through a thin layer of Chromatographic separation and purification to obtain the target product, the stationary phase of the thin-layer chromatography used is silica gel, and the eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate=5:1, v / v), the obtained The yield of product was 84%.

[0079] The hydroge...

Embodiment 3

[0086] The third embodiment of the present invention is: a method for synthesizing imidazolidinone derivatives, comprising the following steps:

[0087] In a schlenk tube, add 0.25 mmol 4-fluorobenzamidine hydrochloride, 0.5 mmol 1,2 cyclohexanediol, 0.5 mmol sodium methoxide, and 60 mg titanium dioxide-supported nano-cobalt catalyst (the mass fraction of titanium dioxide is 3 %) and 1 ml of methanol, stirred and reacted at 120 ° C under air conditions for 10 hours, stopped heating and stirring, cooled to room temperature, evaporated under reduced pressure to remove the solvent, and then separated and purified by thin-layer chromatography to obtain the target product. The stationary phase of thin layer chromatography is silica gel, the eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate=7:1, v / v), and the yield of the obtained product is 83%.

[0088] The hydrogen spectrogram and carbon spectrogram of the product obtained in Example 3 ...

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Abstract

The invention discloses a synthesis method of imidazolinone derivatives. Using amidine compounds and polyols as raw materials, it catalyzes the high-value conversion of polyols into a series of imidazolinone derivatives through cobalt catalysts, and develops a novel, green, and sustainable chemical synthesis route. The high-value conversion of renewable resources is realized, thus meeting the demand for the synthesis of imidazolinone derivatives. This synthetic method has the advantages of wide substrate applicability, good functional group compatibility, and the use of reusable and cheap metal catalysts and air as the oxidant, and has the potential to prepare imidazolinone derivatives on a large scale in one step, and is also an important resource for biomass resources. Conversion into high-value functional molecules provides an important pathway.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing imidazolidinone derivatives. Background technique [0002] Imidazolidinones are a class of nitrogen-containing heterocyclic compounds with good biological and pharmacological activities. They are widely present in natural active products and play an important role in human health and industrial and agricultural production. Many imidazolinone fungicides, herbicides and natural medicines have been discovered. [0003] Owing to their promising properties, the construction of imidazolidinone derivatives has been an attractive topic in the scientific community. Conventional methods for imidazolidinone functional molecules in the related art involve the following reactions: (1) cyclization reaction of diamide compounds; (2) cyclization condensation reaction of amino ester and cyanamide; (3) 1 , The intermolecular condensation reaction of 3-dicarbon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/02C07D401/04C07D233/70
CPCC07D235/02C07D401/04C07D233/70
Inventor 谢锋张向宇林世卓罗楚君陈灵容陈晓勇
Owner WUYI UNIV
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