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2,3-diaryl pyrimidine [1,2-a]benzimidazole heterocyclic compound, preparation and use thereof

A technology of diaryl pyrimidine and benzimidazole, which is applied in the field of heterocyclic compounds, and can solve the problems of difficult control, limitation, and low yield of substitution positions

Inactive Publication Date: 2009-07-22
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when these methods synthesize pyrimidine [1,2-a] benzimidazoles, their synthesis is limited due to limitations such as low yield and difficult control of substitution positions, and so far no one has synthesized 2 , 3-Diarylpyrimidine[1,2-a]benzimidazoles

Method used

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  • 2,3-diaryl pyrimidine [1,2-a]benzimidazole heterocyclic compound, preparation and use thereof
  • 2,3-diaryl pyrimidine [1,2-a]benzimidazole heterocyclic compound, preparation and use thereof
  • 2,3-diaryl pyrimidine [1,2-a]benzimidazole heterocyclic compound, preparation and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] (1) Preparation of compound 1 2-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimidine[1,2-a]benzimidazole.

[0034] In this example, first add 4', 7-dihydroxy isoflavone to the reaction kettle, add methanol with 20 times the weight of 4', 7-dihydroxy isoflavone under stirring, then add sodium methoxide and benzo 2-amino Imidazole, the amount of sodium methylate used is 2 times of the molar weight of the isoflavone compound, the amount of benzo2-aminoimidazole is 3 times of the molar weight of the isoflavone compound, and the temperature of the reaction solution is 65 ℃ with a temperature regulating device, and the reaction is 10 Hour, obtain the mixture of 2-(2,4-dihydroxyphenyl)-3-(4-hydroxylphenyl) pyrimidine [1,2-a] benzimidazole and unreacted substance; Adjust the acidity of the mixture after the reaction To neutrality, add distilled water of 3 times the total volume of the reactant, fully stir, and filter under reduced pressure to obtain the crude product 2-(2,4-dihy...

Embodiment 2

[0144] (1) Preparation of compound 1 2-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimidine[1,2-a]benzimidazole

[0145] In this example, first add 4', 7-dihydroxy isoflavone to the reaction kettle, add methanol with 10 times the weight of 4', 7-dihydroxy isoflavone under stirring, then add sodium methoxide, benzo 2-amino Imidazole, the amount of sodium methylate used is 2 times of the molar weight of the isoflavone compound, and the amount of benzo2-aminoimidazole is 3 times of the molar weight of the isoflavone compound, and the temperature of the reaction solution is 65 ℃ with a temperature regulating device, and the reaction 8 hours, obtain the mixture of 2-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl) pyrimidine [1,2-a] benzimidazole and unreacted substance; Adjust the reacted mixture To neutrality, add 3 times the amount of distilled water of the total volume of the reactant, fully stir, and filter under reduced pressure, the 2-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimid...

Embodiment 3

[0149] (1) Preparation of compound 1 2-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimidine[1,2-a]benzimidazole

[0150] In this example, first add 4', 7-dihydroxy isoflavone to the reaction kettle, add methanol with 20 times the weight of 4', 7-dihydroxy isoflavone under stirring, then add sodium methoxide, benzo 2-amino Imidazole, the amount of sodium methylate used is 1 time of the molar weight of the isoflavone compound, and the amount of benzo2-aminoimidazole is 5 times of the molar weight of the isoflavone compound, and the temperature of the reaction solution is 65 ° C with a temperature regulating device, and the reaction 12 hours, obtain the mixture of 2-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl) pyrimidine [1,2-a] benzimidazole and unreacted substance; Adjust the reacted mixture To neutrality, add 3 times the amount of distilled water of the total volume of the reactant, stir well, and filter under reduced pressure, the 2-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimi...

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Abstract

The invention pertains to the technical field of a heterocyclic compound, in particular relates to an un-hydrogenated heterocyclic compound which contains five / six-membered ring, three nitrogen atoms as heterocycle atoms and other condensed benzene rings. The invention provides 2, 3-diaryl pyrimidine [1, 2-a] benzimidazole compounds which conform to general formula 1; the technology comprises the following steps: a reactant, i.e., isoflavone is added into a solvent; then, a basic catalyst and benzo 2-aminooimidazole are also added into the solvent; the reactant reacts with the 2-aminooimidazole to obtain a mixture of the un-hydrogenated heterocyclic compound and un-reacted materials; and the mixture is re-crystallized for purification so that the pure heterocyclic compound is obtained. The invention also provides a photoluminescence material which can be applied to the preparation of anti-fake labels and modification labels and also can be used as indicators of night road-signs.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and specifically relates to heterocyclic compounds containing five or six-membered rings without hydrogenation, three nitrogen atoms as ring heteroatoms, and other benzene rings condensed. Background technique [0002] Pyrimidine [1,2-a] benzimidazole compounds are uncommon compounds in nature, and the synthetic methods of the basic skeleton pyrimidine [1,2-a] benzimidazoles of this type of compound can be roughly divided into three categories: (1 ) Cycloaddition of 2-aminobenzimidazole compounds and 1,3-dicarbonyl compounds; (2) intramolecular condensation reaction of ortho-halogen carbonyl compounds; (3) 2-aminobenzimidazole compounds and α, β - Cycloaddition of unsaturated carbonyl compounds. However, when these methods synthesize pyrimidine [1,2-a] benzimidazoles, their synthesis is limited due to limitations such as low yield and difficult control of substitution positions, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K9/02C09K11/06
Inventor 张尊听邱李薛东
Owner SHAANXI NORMAL UNIV
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