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

A technology of diarylpyrimidine and benzimidazole, applied in the field of heterocyclic compounds, can solve the problems of low yield, difficult control and limitation of substitution position

Inactive Publication Date: 2011-07-06
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

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Effect test

Embodiment 1

[0032] (1) Preparation of compound 12-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimidine[1,2-a]benzimidazole.

[0033] 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-dihyd...

Embodiment 2

[0143] (1) Preparation of compound 12-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimidine[1,2-a]benzimidazole

[0144] 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, stir well, and filter under reduced pressure, the 2-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimidin...

Embodiment 3

[0148] (1) Preparation of compound 12-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)pyrimidine[1,2-a]benzimidazole

[0149] 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)pyrimid...

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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 thefollowing 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 Patents(China)
IPC IPC(8): C07D487/04C09K9/02C09K11/06
Inventor 张尊听邱李薛东
Owner SHAANXI NORMAL UNIV
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