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Method for constructing 2-(2-naphthyl)imidazole[1,2-a]pyridine-3-nitrile by taking DMF and ammonium iodide as cyanation reagents

An ammonium iodide, 2-a technology, applied in the fields of materials, cell biology, and medicine, can solve problems such as environmental pollution, potential safety hazards, and abnormal inconvenience in post-processing processes, and achieve novel synthesis methods, mild reaction conditions, and reagents. Inexpensive and accessible effects

Inactive Publication Date: 2019-11-12
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional cyanation reagents, such as sodium cyanide, potassium cyanide, copper cyanide, and zinc cyanide, often generate highly toxic hydrogen cyanide during the cyanation process, causing serious environmental pollution. The post-processing process is extremely inconvenient, and there is a great potential safety hazard

Method used

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  • Method for constructing 2-(2-naphthyl)imidazole[1,2-a]pyridine-3-nitrile by taking DMF and ammonium iodide as cyanation reagents
  • Method for constructing 2-(2-naphthyl)imidazole[1,2-a]pyridine-3-nitrile by taking DMF and ammonium iodide as cyanation reagents
  • Method for constructing 2-(2-naphthyl)imidazole[1,2-a]pyridine-3-nitrile by taking DMF and ammonium iodide as cyanation reagents

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 0.2 mmol of compound 2-(2-naphthyl)imidazol[1,2-a]pyridine, 0.4 mmol of copper nitrate trihydrate, 0.4 mmol of ammonium iodide, 0.4 mmol of acetic acid, and add N , 2 ml of N-dimethylformamide (DMF) was used as a reaction solvent, covered with a balloon filled with oxygen, and stirred at 130 degrees Celsius. After TLC (thin-layer chromatography) detection, the reaction solution was cooled to room temperature, the balloon was removed, and unreacted oxygen was slowly vented. The reaction solution was filtered, the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the compound 2-(2-naphthyl)imidazo[1,2-a]pyridine-3-carbonitrile, the yield of this step was 78% .

Embodiment 2

[0025] Add 0.2 mmol of compound 2-(2-naphthyl)imidazol[1,2-a]pyridine, 0.4 mmol of copper acetate, 0.4 mmol of ammonium iodide, 0.4 mmol of acetic acid into a 25mL test tube, add N,N - Dimethylformamide (DMF) 2 milliliters is used as the reaction solvent, put on a balloon filled with oxygen, and stir at 130 degrees Celsius. After TLC (thin-layer chromatography) detection, the reaction solution was cooled to room temperature, the balloon was removed, and unreacted oxygen was slowly vented. The reaction solution was filtered, the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the compound 2-(2-naphthyl)imidazo[1,2-a]pyridine-3-carbonitrile, the yield of this step was 12% .

Embodiment 3

[0027] In a 25mL test tube, add 0.2 mmol of compound 2-(2-naphthyl)imidazol[1,2-a]pyridine, 0.4 mmol of copper bromide, 0.4 mmol of ammonium iodide, 0.4 mmol of acetic acid, add N, 2 ml of N-dimethylformamide (DMF) was used as a reaction solvent, covered with a balloon filled with oxygen, and stirred at 130 degrees Celsius. TLC (thin layer chromatography) tracking detection, no target product was detected.

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Abstract

The invention discloses a new method for one-step constructing 2-(2-naphthyl)imidazole[1,2-a]pyridine-3-nitrile by taking DMF(N,N-dimethylformamide) and ammonium iodide as cyanation reagents. According to the method, 2-(2-naphthyl)imidazole[1,2-a]pyridine is used as a reaction raw material, and the DMF(N,N-dimethylformamide) and the ammonium iodide are used as the cyanation reagents to construct the 2-(2-naphthyl)imidazole[1,2-a]pyridine-3-nitrile in one step; and the synthesis way is novel, reaction conditions are mild, the reaction reagents are cheap and easy to get, the N,N-dimethylformamide can be used as a reaction solvent and the cyanation reagent to supply carbon atoms in cyan, the ammonium iodide supplies nitrogen atoms in the cyan, and the cyanide source of combination is safe andnon-toxic, and the development requirements for green chemistry are met.

Description

technical field [0001] The invention belongs to the technical fields of medicine, materials, cell biology, etc., and specifically relates to a one-step construction of 2-(2-naphthyl) by using DMF (N,N-dimethylformamide) and ammonium iodide as cyanation reagents ) A new method for imidazo[1,2-a]pyridine-3-carbonitriles. Background technique [0002] 2-(2-Naphthyl)imidazo[1,2-a]pyridine-3-carbonitrile compounds are a very important class of pharmaceutical intermediates, which can be used to synthesize various pharmaceutically active drug molecules. The contained structural skeleton can be used as the starting material to construct the familiar drug molecules sapiridan with antidepressant effect and necopiridan with anesthetic effect. Traditional cyanation reagents, such as sodium cyanide, potassium cyanide, copper cyanide, and zinc cyanide, often generate highly toxic hydrogen cyanide during the cyanation process, causing serious environmental pollution. It makes the post-pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 及方华王守才蒋光彬
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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