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Synthesizing method of pyridino imidazo [1,2,3] triazoloquinoline compound

A pyridoimidazole and synthetic method technology, applied in the direction of organic chemistry, etc., can solve the problems of difficult to obtain raw materials, poor atom economy, and many reaction steps, and achieve the effects of easy preparation, avoiding waste of resources, and simple reaction operation

Active Publication Date: 2016-10-26
HENAN NORMAL UNIV
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  • Abstract
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AI Technical Summary

Problems solved by technology

The only synthesis method of this kind of compound is through copper catalyzed 3-bromo-2-(2-bromophenyl)imidazol[1,2- a ]pyridine with alkynes and sodium azide cycloaddition and coupling reactions (Pericherla, K.; Jha, A.; Khungar, B.; Kumar, A. Org. Lett. 2013, 15 , 4304.), although this method is more effective, the raw material 3-bromo-2-(2-bromophenyl)imidazol[1,2- a ]pyridine needs to be replaced with 2-(2-bromophenyl)imidazol[1,2- a ]pyridine is obtained by bromination reaction as a raw material, so there are still disadvantages such as raw materials are not easy to obtain, many reaction steps, poor atom economy and low environmental factors

Method used

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  • Synthesizing method of pyridino imidazo [1,2,3] triazoloquinoline compound
  • Synthesizing method of pyridino imidazo [1,2,3] triazoloquinoline compound
  • Synthesizing method of pyridino imidazo [1,2,3] triazoloquinoline compound

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Experimental program
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Effect test

Embodiment 1

[0013]

[0014] Add 1a (0.5 mmol, 137 mg), DMF (3 mL), 2a (0.6 mmol, 61 mg), 3 (0.6 mmol, 39 mg), CuI (0.05 mmol, 10 mg) and K in a 10 mL round bottom flask 2 CO 3 (0.6 mmol, 83 mg). The flask was placed in an oil bath at 120 °C, stirred for 6 h, and cooled to room temperature. Then, add Pd(OAc) to the reaction system 2 (0.025 mmol, 6 mg) and Cu(OAc) 2 (0.5 mmol, 91 mg), and the reaction bottle was placed in an oil bath at 120 °C again, and the reaction was stirred for 7 h. The reaction was quenched by adding 10 mL of saturated ammonium chloride solution, extracted with ethyl acetate (6 mL × 3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate=1 / 1) gave the target product 4a (42 mg, 25%). The characterization data of this compound are as follows: 1 H NMR (400MHz, d 1 -TFA) δ 6.99 (t, J = 6.8 Hz, 1H), 7...

Embodiment 2

[0016] Add 1a (0.5 mmol, 137 mg), DMF (3 mL), 2a (0.6 mmol, 61 mg), 3 (0.6 mmol, 39 mg), CuI (0.05 mmol, 10 mg) and K in a 10 mL round bottom flask 2 CO 3 (0.6 mmol, 83 mg). The flask was placed in an oil bath at 120 °C, stirred for 6 h, and cooled to room temperature. Then, add Pd(OAc) to the reaction system 2 (0.025 mmol, 6 mg), AcOH (0.5 mmol, 30 mg) and Cu(OAc) 2 (0.5 mmol, 91 mg), and the reaction bottle was placed in an oil bath at 120 °C again, and the reaction was stirred for 7 h. The reaction was quenched by adding 10 mL of saturated ammonium chloride solution, extracted with ethyl acetate (6 mL × 3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate=1 / 1) gave the target product 4a (60 mg, 36%).

Embodiment 3

[0018] Add 1a (0.5 mmol, 137 mg), DMF (3 mL), 2a (0.6 mmol, 61 mg), 3 (0.6 mmol, 39 mg), CuI (0.05 mmol, 10 mg) and K in a 10 mL round bottom flask 2 CO 3 (0.6 mmol, 83 mg). The flask was placed in an oil bath at 120 °C, stirred for 6 h, and cooled to room temperature. Then, add Pd(OAc) to the reaction system 2 (0.025 mmol, 6 mg), AcOH (1 mmol, 60 mg) and Cu(OAc) 2(0.5 mmol, 91 mg), and the reaction bottle was placed in an oil bath at 120 °C again, and the reaction was stirred for 7 h. The reaction was quenched by adding 10 mL of saturated ammonium chloride solution, extracted with ethyl acetate (6 mL × 3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=1 / 1) to obtain the target product 4a (97 mg, 58%).

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Abstract

The invention discloses a synthesizing method of a pyridino imidazo [1,2,3] triazoloquinoline compound. The synthesizing method includes: dissolving 2-(2-bromophenyl) imidazole [1,2-a] pyridine or the derivatives and polyacetylenes of 2-(2-bromophenyl) imidazole [1,2-a] pyridine and sodium azide into N, N-dimethyl formamide, adding copper iodide and potassium carbonate, reacting at 120 DEG C for 6 hours, adding transition metal salt catalyst and additives or / and oxidizing agent, reacting at 80-130 DEG C to obtain a pyridine [2',1':2,3] imidazole [4,5-c] [1,2,3] triazole [1,5-a] quinoline compound. The synthesizing method has the advantages that the pyridino imidazo [1,2,3] triazoloquinoline compound is obtained in a one-pot two-step manner through the tandem reaction under bimetallic catalysis, a quinoline ring and a 1,2,3-triazole ring are built in the one-pot reaction, heterocyclic ring structural units such as pyridino imidazole, 1,2,3-triazole and quinoline are condensed together to directly obtain a five-ring aromatic system, high efficiency is achieved, and resource waste and environment pollution caused by the purification of reaction intermediate in the literature method are avoided.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of pyridoimidazo[1,2,3]triazoloquinoline compounds. Background technique [0002] 1,2,3-Triazole occupies an important position in the field of medicinal chemistry. Many organic molecules containing this structural unit have shown good drug activities such as inhibiting HIV protease, anticancer, antituberculosis and antifungal. In addition, due to its stability to metabolic degradation and good hydrogen bond formation ability, 1,2,3-triazole is also an ideal linking unit in the design of drug molecules. On the other hand, pyridimidazole is not only the basic skeleton of many antiviral, antibacterial, anticancer and nerve tissue stimulating drugs, but also widely used in the fields of biological probes, fluorescent dyes and optoelectronic materials, showing broad application prospects . The pyridoimidazo[1,2,3]triazoloquinoline compound s...

Claims

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Application Information

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IPC IPC(8): C07D471/22
CPCC07D471/22
Inventor 范学森李彬王泽张新迎郭胜海
Owner HENAN NORMAL UNIV
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