Preparing method for C-3 position sulfoimidazo[1,2-a] pyridine compound

A technology for thioimidazoles and compounds, which is applied in the field of preparation of C-3 thioimidazo[1,2-a]pyridine compounds, which can solve the need to deal with the reaction solvent, the reaction substrate is volatile, and the reaction conditions are harsh and other problems, to achieve the effect of convenient separation and purification, less environmental pollution, and mild reaction conditions

Active Publication Date: 2016-01-06
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

In recent years, some foreign research groups have also reported some methods of synthesizing C-3 thioimidazopyridine compounds, but these methods have obvious shortcomi

Method used

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  • Preparing method for C-3 position sulfoimidazo[1,2-a] pyridine compound
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  • Preparing method for C-3 position sulfoimidazo[1,2-a] pyridine compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] At room temperature, add NaI (0.06 mmol), 2-(4-chlorophenyl)imidazo[1,2- a ] pyridine (0.3mmol) and benzenesulfonylhydrazide (0.6mmol), TBHP (0.6mmol, 70% mass fraction in water), then add 2ml of acetonitrile, vacuum the tube twice and backfill with nitrogen, seal the tube with a balloon, Then the mixture was stirred under nitrogen atmosphere and reacted at 90°C for 18h. After the reaction was complete, the resulting solution was cooled to room temperature, and the solvent was removed with a rotary evaporator. The residue was purified with a silica gel column (silica gel specification 200-300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain 2-(4-chlorophenyl)-3- (Phenylthio)imidazo[1,2- a ] Pyridine 0.078g, productive rate is 77%.

[0036] 1 HNMR (CDCl 3 ,400MHz,ppm) δ 8.28(d,1H, J =8.0Hz),8.20(d,2H, J =8.0Hz),7.74(d,1H, J =8.0Hz),7.42(d,2H, J =8.0Hz),7.36(t,1H,J =16.0Hz),7.23(t,2H, J =16.0Hz),7.16(t,1H, J =16.0Hz)7.00(d,2H, J =...

Embodiment 2

[0038]

[0039] At room temperature, add NaI (0.06 mmol), 2-(4-chlorophenyl)imidazo[1,2- a ]pyridine (0.3mmol) and p-toluenesulfonylhydrazide (0.6mmol), TBHP (0.6mmol, 70% mass fraction in water), then 2ml of acetonitrile was added, the tube was evacuated twice and backfilled with nitrogen, and the tube was sealed with a balloon , and then the mixture was stirred under a nitrogen atmosphere and reacted at 90° C. for 18 h. After the reaction was complete, the resulting solution was cooled to room temperature, and the solvent was removed with a rotary evaporator. The residue was purified with a silica gel column (silica gel specification 200-300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain 2-(4-chlorophenyl)-3- (p-Tolylthio)imidazo[1,2- a ] Pyridine 0.076g, productive rate is 72%.

[0040] 1 HNMR (CDCl 3 ,400MHz,ppm) δ 8.29(d,1H, J =8.0Hz),8.22(d,2H, J =8.0Hz),7.73(d,1H, J =8.0Hz),7.42(d,2H, J =8.0Hz),7.34(t,1H, J =16.0Hz),7.04(d,2H, J =8.0Hz)...

Embodiment 3

[0042]

[0043] At room temperature, add NaI (0.06 mmol), 2-(4-chlorophenyl)imidazo[1,2- a ]pyridine (0.3mmol) and p-bromobenzenesulfonyl hydrazide (0.6mmol), TBHP (0.6mmol, 70% aqueous solution by mass fraction), and then add 2ml of acetonitrile, vacuum the tube twice and backfill it with nitrogen, and balloon the tube After sealing, the mixture was stirred under a nitrogen atmosphere and reacted at 90°C for 18h. After the reaction was complete, the resulting solution was cooled to room temperature, and the solvent was removed with a rotary evaporator. The residue was purified with a silica gel column (silica gel specification 200-300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain 3-(4-bromophenylthio)-2 -(4-Chlorophenyl)imidazo[1,2- a ] Pyridine 0.094g, productive rate is 76%.

[0044] 1 HNMR (CDCl 3 ,400MHz,ppm) δ 8.26(d,1H, J =8.0Hz),8.15(d,2H, J =8.0Hz),7.75(d,1H, J =8.0Hz),7.43-7.33(m,5H),6.93(t,1H, J =8.0Hz),6.86(d,2H, J =8.0Hz). 13 CNM...

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Abstract

The invention discloses a preparing method for a C-3 position sulfoimidazo[1,2-a] pyridine compound. The preparing method includes the step that an imidazo[1,2-a] pyridine compound and a sulfohydrazide compound serving as raw materials, tert-butyl hydroperoxide serving as an oxidizing agent, acetonitrile serving as solvent, and an iodine compound serving as a catalyst react at the reaction temperature of 60 DEG C-120 DEG C to obtain the C-3 position sulfoimidazo[1,2-a] pyridine compound. Compared with a traditional synthetic method, the preparing method has the advantages that reaction conditions are moderate, environment pollution is little, reaction smells are small, the yield is high, functional group compatibility is high, and separation and purification are convenient.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of C-3 thioimidazo[1,2-a]pyridine compounds. Background technique [0002] Imidazo[1,2-a]pyridine compounds widely exist in many natural products and biologically active compounds, and have a wide range of biological activities. Such as: antipyretic, bactericidal, anticancer, antiviral, sleeping, and as an insecticide. Many commercial drugs also contain this structure, such as: Oprinone, Minodronic Acid, Zolimidine, Alpitant, Zolpidem, Necopitant, etc. Based on the importance of these compounds, the methods for the diversified synthesis of imidazo[1,2-a]pyridine compounds need to be further developed. [0003] It is well known that the biological activity of compounds mainly depends on the structure of functional groups. The introduction of a thiol group at the C-3 position of imidazo[1,2-a]pyridine compounds will improve the biological activity of ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 王桦闫克鲁杨道山
Owner QUFU NORMAL UNIV
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