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Imidazo[1,2-alpha] pyridine derivative, preparation method thereof and application thereof to color changing powder

An imidazo, derivative technology, applied in the application of fluorescent dyes, preparation, color-changing powder and biological reagents, in the field of imidazo[1,2-α]pyridine derivatives, can solve problems such as no literature reports, and achieve preparation The method is simple, the yield is high, and the substrate is suitable for a wide range of effects.

Active Publication Date: 2019-03-08
SHANGHAI GANTIAN OPTICAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the 8-position of 2-arylimidazo[1,2-α]pyridine is substituted with phenyl to realize 8-phenylphenanthrene[9',10':4,5]imidazo [1,2-α]pyridine derivatives have not been reported

Method used

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  • Imidazo[1,2-alpha] pyridine derivative, preparation method thereof and application thereof to color changing powder
  • Imidazo[1,2-alpha] pyridine derivative, preparation method thereof and application thereof to color changing powder
  • Imidazo[1,2-alpha] pyridine derivative, preparation method thereof and application thereof to color changing powder

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Experimental program
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Effect test

Embodiment 1

[0049]

[0050] Mix 2-phenylimidazo[1,2-α]pyridine (compound II-1, 0.2mmol, 1 equivalent) and palladium acetate (0.02mmol, 10mol% equivalent), add 4mL of acetic acid as a solvent, and then add benzene Base iodide (compound III-1, 0.6 mmol, 3 equivalents), dipotassium hydrogen phosphate (0.4 mmol, 2 equivalents), react at 110°C for 24 hours, cool to room temperature, neutralize acetic acid with aqueous sodium bicarbonate, dichloro Methane extraction, separation and purification by dry loading column chromatography (eluent: petroleum ether: ethyl acetate = 5:1) gave the target product (compound I-1) as a white solid with a yield of 83%. 1 H NMR (400MHz, CDCl 3 )δ 9.11(d, J=7.1Hz, 1H), 8.92(d, J=8.3Hz, 1H), 8.81(d, J=8.2Hz, 1H), 8.53(d, J=8.1Hz, 1H), 7.77(t,J=7.7Hz,1H),7.75–7.70(m,1H),7.67(t,J=7.4Hz,1H),7.61(d,J=6.7Hz,1H),7.57 (ddd,J =14.4,8.4,6.1Hz,3H),7.52–7.44(m,3H),7.26(dd,J=8.9,6.4Hz,1H),6.96(t,J=6.4Hz,1H).

Embodiment 2

[0052]

[0053] Mix 2-(4-fluorophenyl)imidazo[1,2-α]pyridine (compound II-2, 0.2mmol, 1 equivalent) and palladium acetate (0.02 mmol, 10mol% equivalent), add 4mL of acetic acid as Solvent, then add phenyl iodide (compound III-1, 0.6 mmol, 3 equivalents), dipotassium hydrogen phosphate (0.4 mmol, 2 equivalents), react at 110 ° C for 24 hours, cool to room temperature, and use sodium bicarbonate aqueous solution and acetic acid, dichloromethane extraction, dry loading column chromatography separation and purification (eluent: petroleum ether: ethyl acetate = 5:1), to obtain the white solid target product (compound I-2), yield 70% . 1 H NMR (400MHz, DMSO) δ9.53(d, J=7.0Hz, 1H), 9.04(d, J=8.3Hz, 1H), 8.83(d, J=8.2Hz, 1H), 8.79(dd, J = 11.6,2.3Hz,1H),7.87(t,J=7.6Hz,1H),7.71(t,J=7.7Hz,1H),7.51–7.35(m,8H),7.14(dd,J=9.2, 3.8Hz,1H).

Embodiment 3

[0055]

[0056] Mix 2-(4-chlorophenyl)imidazo[1,2-α]pyridine (compound II-3, 0.2mmol, 1 equivalent) and palladium acetate (0.02 mmol, 10mol% equivalent), add 4 mL of acetic acid for Solvent, then add phenyl iodide (compound III-1, 0.6 mmol, 3 equivalents), dipotassium hydrogen phosphate (0.4 mmol, 2 equivalents), react at 110 ° C for 24 hours, cool to room temperature, and use sodium bicarbonate aqueous solution and acetic acid, dichloromethane extraction, dry loading column chromatography separation and purification (eluent: petroleum ether: ethyl acetate = 5:1), to obtain the white solid target product (compound I-3), yield 66% . 1 H NMR (400MHz, DMSO) δ9.56(d, J=7.1Hz, 1H), 9.12(d, J=8.1Hz, 1H), 9.05(d, J=2.1Hz, 1H), 8.86(d, J = 8.1Hz,1H),7.90(t,J=7.3Hz,1H),7.74(t,J=7.4Hz,1H),7.53(d,J=2.0Hz,1H),7.49–7.41 (m,7H ),7.22–7.13(m,1H).

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Abstract

The invention discloses an imidazo[1,2-alpha] pyridine derivative. The structure of the imidazo[1,2-alpha] pyridine derivative is expressed as a formula which is as shown in description; in the formula I, R1, R2 and R3 are respectively and independently selected from hydrogen, halogen, alkyl, alkoxy, halogen-substituted alkyl, halogen-substituted alkoxy, aryl and substituted aryl. The imidazo[1,2-alpha] pyridine derivative is simple in preparation method and is nontoxic and harmless; the imidazo[1,2-alpha] pyridine derivative is capable of emitting blue luminescent light in solution and solidphase and can be used as a potential organic functional pigment material, a color changing powder intermediate, a fluorescent material and an electronic information material.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to an imidazo[1,2-α]pyridine derivative, a preparation method and its application in fluorescent dyes, color-changing powders and biological reagents. Background technique [0002] Phenanthrene[9',10':4,5]imidazo[1,2-α]pyridine derivatives are an important class of aromatic compounds. These compounds have now been found to be useful in electroluminescent devices or other applications. Similar conjugated polyaromatic hydrocarbons have likewise been extensively studied because their unusual π-systems have been used in biological probes, functional dyeing materials, organic light-emitting diodes, light-harvesting arrays, and organic electronic devices (Wong, H.N.C. et al.; Asian J. Org. Chem. 2017, 6, 1876-1884). [0003] The phenanthrene[9',10':4,5]imidazo[1,2-α]pyridine skeleton is a class of molecules with important applications in the field of materials scien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06
CPCC07D471/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044
Inventor 韩建伟甘家安程毅
Owner SHANGHAI GANTIAN OPTICAL MATERIALS