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Synthetic method for semi-cucurbituril [6] with 2-imidazolidone and derivatives therefor as unit

A technology of imidazolidinone and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of difficulty in synthesizing cucurbituril derivatives with adjustable structure and biological activity, lack of functional group modification sites, etc.

Inactive Publication Date: 2013-10-30
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Due to the rigid structure of cucurbituril and the lack of functional group modification sites for further functionalization, it is difficult to synthesize cucurbituril derivatives with adjustable structure and biological activity

Method used

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  • Synthetic method for semi-cucurbituril [6] with 2-imidazolidone and derivatives therefor as unit
  • Synthetic method for semi-cucurbituril [6] with 2-imidazolidone and derivatives therefor as unit
  • Synthetic method for semi-cucurbituril [6] with 2-imidazolidone and derivatives therefor as unit

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Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1: Hydrochloric acid catalyzes half cucurbituril [6] synthetic method

[0027] Cucurbituril was synthesized using 2-imidazolidinone as a five-membered urea ring unit and formaldehyde in a 2mol / L hydrochloric acid system [6]. 4.00 g of 2-imidazolidinone with a content of 99% and 1.1 g of paraformaldehyde with a content of 94% were weighed respectively, the reaction temperature was 70° C., and the reaction time was 10 hours to obtain a white solid with a yield of 72%. The chemical reaction formula is as follows:

[0028]

Embodiment 2

[0029] Embodiment 2: Sulfuric acid catalyzes half cucurbituril [6] synthetic method

[0030] Cucurbituril was synthesized using 2-imidazolidinone as a five-membered urea ring unit and formaldehyde in a 2mol / L sulfuric acid system [6]. 4.00 g of 2-imidazolidinone with a content of 99% and 1.1 g of paraformaldehyde with a content of 94% were weighed respectively, the reaction temperature was 70° C., and the reaction time was 10 hours to obtain a white solid with a yield of 83%.

Embodiment 3

[0031] Embodiment 3: Acetic acid catalyzes half cucurbituril [6] synthetic method

[0032] Cucurbituril was synthesized using 2-imidazolidinone as a five-membered urea ring unit and formaldehyde in a 4mol / L hydrochloric acid system [6]. 4.00 g of 2-imidazolidinone with a content of 99% and 1.1 g of paraformaldehyde with a content of 94% were weighed respectively, the reaction temperature was 60° C., and the reaction time was 10 hours to obtain a white solid with a yield of 68%.

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Abstract

The invention provides a synthetic method for semi-cucurbituril [6] with 2-imidazolidone and derivatives therefor as a unit. Semi-cucurbituril is a six-membered polymerization ring with a structure similar to half structure of unit glycoluril for synthesis of cucurbituril as a unit, namely, with 2- imidazolidone as a unit, also named after semi-cucurbituril [6], and is an organic heterocyclic compound. The synthetic method employs 2-imidazolidone, derivatives therefor, and formaldehyde as raw materials. The raw materials are subjected to heating reflux for 4-24 h in an acidic aqueous solution system at the temperature of 40- 80 DEG C, and then subjected to condensation, filtration, isolation and purification to obtain semi-cucurbituril [6]. The material molar ratio of 2-imidazolidone and derivatives therefor to formaldehyde is 1:1-1.2. The catalytic acidic system can be inorganic acids or organic acids, with a concentration range from pH=2 to 5 mol / L. Semi-cucurbituril [6] can be synthetised with inorganic salts and ionic liquids as template agents. Semi-cucurbituril [6] with single component can be synthetised through control of conditions such as concentration of the reactants, acidity and temperature of the reaction system and the like.

Description

【Technical field】 [0001] The present invention uses 2-imidazolidinone and its derivative unit ring and formaldehyde as reactants to reflux reaction under certain temperature and acidity conditions to generate hemicucurbituril[6]. 【Background technique】 [0002] Cucurbituril [6] has a rigid cavity with small ends and a large middle. The diameter of the cavity of cucurbituril [6] is similar to the diameter of the two ports of α-cyclodextrin. Its structure has good rigidity, and the cavity has Hydrophobic, capable of accommodating molecules of appropriate size, the ports are arranged with symmetrical and ordered carbonyl groups, forming a good bonding site, which can bond metal ions or organic compounds through ion-dipole interactions and hydrogen bonding with carbonyl groups The charged part of a molecule. It has a strong and specific inclusion effect on specific structures. Cucurbituril [6] is insoluble in water and common organic solvents, but suitable for soluble in acidi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
Inventor 薛红郭琦童张法周希波何熙璞刘旭刘真珍
Owner GUANGXI UNIV
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