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2,3-disubstituted benzimidazo[1,2-alpha]pyrimidine compound and preparation method and application thereof

A technology for benzimidazoles and compounds is applied in the application field of detecting Fe3+, which can solve the problems of harsh reaction conditions, long steps, limited scope of application of substrates, etc., and achieves the effect of wide application scope and simplified operation.

Active Publication Date: 2018-07-06
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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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-alpha]pyrimidine compound and preparation method and application thereof
  • 2,3-disubstituted benzimidazo[1,2-alpha]pyrimidine compound and preparation method and application thereof
  • 2,3-disubstituted benzimidazo[1,2-alpha]pyrimidine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Place 2-aminobenzimidazole (133mg, 1mmol), cuprous iodide (19mg, 0.1mmol), potassium carbonate (165mg, 1.2mmol) in a sealed tube, and add nothing to the sealed tube under an argon atmosphere. Water dimethyl sulfoxide (4mL), benzaldehyde (0.21mL, 2.1mmol), propiolic acid (74μL, 1.2mmol), stir the reaction at 110°C for 12 hours, cool to room temperature, add dichloromethane to dilute, and use Wash with distilled water, saturated aqueous ammonium chloride, saturated brine, back-extract and combine the organic phases, dry with anhydrous sodium sulfate, concentrate, and separate by column chromatography (the eluent is: petroleum ether and ethyl acetate in a volume ratio of 2:1 Triethylamine (1% of the volume of the mixed solution) is added to the mixed solution to obtain 217 mg of 2-phenyl-3-benzimidazo[1,2-a]pyrimidine with a yield of 65%. The reaction equation is as follows:

[0035]

[0036] The characterization data of the obtained product are: 1 H NMR(400MHz, CDCl 3 )δ8.35...

Embodiment 2

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

[0039]

[0040] The characterization data of the obtained 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, ; 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, the benzaldehyde in Example 1 is replaced with an equimolar 3-methylbenzaldehyde, and the other steps are the same as in Example 1, to obtain 2-(3-methylphenyl)-3-(3-methyl Benzyl) benzimidazo[1,2-a]pyrimidine 232mg, the yield is 64%, the reaction equation is as follows:

[0043]

[0044] The characterization data of the obtained 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 = 7.6 Hz, 1H), 7.20 (t, J = 7.6 Hz, 1H), 7.07 (d, J = 7.6 Hz, 1H), 6.88 (d, J = 8.0 Hz, 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-H : 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 2,3-disubstituted benzimidazo[1,2-a]pyrimidine compound, a one-pot method for synthesizing the compound and the compound in the detection of Fe 3+ In the application. Background technique [0002] Iron is the second 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 metal enzymes, and is very important for enhancing the body’s immune function. Physiological effects. Although the content is very small, it is inextricably linked with life-sustaining activities and health. When the iron content in the organism is higher or lower than the normal level, it will cause many physiological process disorders, and then cause certain 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 orga...

Claims

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Application Information

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IPC IPC(8): C07D487/04C09K11/06G01N21/64
Inventor 张琦雒欢吴佳荣柴永海
Owner SHAANXI NORMAL UNIV
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