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2,3-Disubstituted benzimidazo[1,2-a]pyrimidine compounds and preparation method and application thereof

A technology of benzimidazoles and compounds, applied in the application field of Fe3+ detection, can solve the problems of harsh reaction conditions, long steps, limited scope of application of substrates, etc., and achieve the effect of wide application range and simplified operation

Active Publication Date: 2019-10-25
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material of this method needs further preparation, and the productive rate is not high
[0011] In summary, the existing literature reports are mostly conventional 2,4-disubstituted benzimidazolo[1,2-a]pyrimidine compounds, and the methods of these compounds have more or less deficiencies in one way or another. , or the raw materials need to be further synthesized, or the scope of application of the substrate is limited or the reaction conditions are harsh, and the steps are long, etc.

Method used

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  • 2,3-Disubstituted benzimidazo[1,2-a]pyrimidine compounds and preparation method and application thereof
  • 2,3-Disubstituted benzimidazo[1,2-a]pyrimidine compounds and preparation method and application thereof
  • 2,3-Disubstituted benzimidazo[1,2-a]pyrimidine compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 2-aminobenzimidazole (133mg, 1mmol), cuprous iodide (19mg, 0.1mmol), potassium carbonate (165mg, 1.2mmol) were placed in a sealed tube, and under an argon atmosphere, no Water dimethyl sulfoxide (4mL), benzaldehyde (0.21mL, 2.1mmol), propiolic acid (74μL, 1.2mmol), stirred and reacted at 110°C for 12 hours, cooled to room temperature, added dichloromethane to dilute, and washed with Wash with distilled water, saturated ammonium chloride aqueous solution and saturated brine, back extract the combined organic phase, dry over anhydrous sodium sulfate, concentrate, and separate by column chromatography (the eluent is: the volume ratio of petroleum ether to ethyl acetate is 2:1 1% of the volume of the mixed solution (triethylamine) was added to the mixed solution to obtain 217 mg of 2-phenyl-3-benzylbenzimidazolo[1,2-a]pyrimidine with a yield of 65%. The reaction equation is as follows:

[0035]

[0036] The characterization data of the resulting product are: 1 H NMR (40...

Embodiment 2

[0038] In this example, replace the benzaldehyde in Example 1 with equimolar 2-methylbenzaldehyde, and the other steps are the same as in Example 1 to obtain 2-(2-methylphenyl)-3-(2-methyl Benzyl) benzimidazolo [1,2-a] pyrimidine 127 mg, yield 35%, the reaction equation is as follows:

[0039]

[0040] The characterization data of the resulting product are: 1 H NMR (400MHz, CDCl 3 )δ8.09(s, 1H), 7.99(d, J=8.4Hz, 1H), 7.71(d, J=8.4Hz, 1H), 7.53(t, J=7.8Hz, 1H), 7.37-7.34( m,2H),7.33(s,1H),7.30(d,J=7.6Hz,1H),7.27-7.25(m,1H),7.23-7.16(m,3H),7.05(d,J=7.2Hz ,1H),3.76(s,2H),2.21(s,3H),2.07(s,3H); 13 C NMR (100MHz, CDCl 3 )δ167.14,149.99,144.76,137.72,136.34,135.63,135.43,131.46,130.80,130.61,130.00,129.03,127.72,127.40,126.78,126.48,126.15,125.75,121.61,120.60,119.32,110.53,33.83,19.46,19.28 ;ESI-HRMS: calculated value C 25 h 21 N 3 ([M+H] + )364.1814, the measured value is 364.1824.

Embodiment 3

[0042] In this example, replace the benzaldehyde in Example 1 with equimolar 3-methylbenzaldehyde, and other steps are the same as in Example 1 to obtain 2-(3-methylphenyl)-3-(3-methyl Benzyl) benzimidazolo [1,2-a] pyrimidine 232mg, yield 64%, reaction equation is as follows:

[0043]

[0044] The characterization data of the resulting product are: 1 H NMR (400MHz, CDCl 3 )δ8.34(s, 1H), 7.99(d, J=8.4Hz, 1H), 7.77(d, J=8.4Hz, 1H), 7.54(t, J=7.8Hz, 1H), 7.41-7.32( m,4H),7.28(d,J=7.6Hz,1H),7.20(t,J=7.6Hz,1H),7.07(d,J=7.6Hz,1H),6.88(d,J=8.0Hz, 1H), 6.85(s,1H), 4.06(s,2H), 2.39(s,3H), 2.30(s,3H); 13 C NMR (100MHz, CDCl 3 )δ166.05,150.13,144.99,138.56,138.46,138.21,138.06,132.63,130.22,129.63,128.71,128.07,127.61,126.11,125.90,125.82,121.52,120.48,118.99,110.59,36.52,21.38,21.32;ESI-HRMS : Calculated value C 25 h 21 N 3 ([M+H] + )364.1814, the measured value is 364.1820.

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Abstract

The invention discloses a 2,3-disubstituted benzimidazo[1,2-alpha]pyrimidine compound and a preparation method and the application thereof. The compound adopts a structural formula as shown in the specification, wherein R represents any one of phenyl, C1-C4 alkyl-substituted phenyl, C1-C4 alkoxy-substituted phenyl, halogenated phenyl, cyano-substituted phenyl, thienyl and naphthyl. The compound isprepared from aromatic aldehyde, 2-aminobenzimidazole and propiolic acid as raw materials by a one-pot method under the coaction of a copper catalyst and an alkaline additive. A synthesis method is simple, intermediate separation is not required, operating steps are simplified, and the application range of a substrate is relatively wide. The compound has fluorescence performance and can be applied to selective fluorescent detection of low-concentrations of Fe<3+>.

Description

technical field [0001] The present invention relates to a kind of 2,3-disubstituted benzimidazolo [1,2-a] pyrimidine compound, and the method for synthesizing the compound and the compound in detecting Fe 3+ in the application. Background technique [0002] Iron is the second most abundant metal element in the earth's crust. As an essential trace element in organisms, it participates in the transportation and storage of oxygen, the synthesis of cytochromes and various metalloenzymes, and has very important functions such as enhancing the body's immune function. Physiological effect. Although the content is very small, it is inextricably linked with maintaining life activities and health. High or low levels of iron in organisms can disrupt many physiological processes, leading to diseases such as anemia, liver and kidney damage, heart disease, and diabetes. Therefore, how to timely and effectively monitor and analyze the content of iron ions in organisms and in the environ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06G01N21/64
CPCC07D487/04C09K11/06C09K2211/1044C09K2211/1092G01N21/6428G01N21/6486G01N2021/6432
Inventor 张琦雒欢吴佳荣柴永海
Owner SHAANXI NORMAL UNIV