Synthesis method and application of imidazole-1,2-dione heterocyclic compounds
A technology of heterocyclic compounds and synthesis methods, which is applied in the field of new synthesis of 1,2-diketone imidazole heterocyclic compounds, can solve the problems of cost and atom economy improvement, and achieve mild reaction conditions, high reaction efficiency, and atomic Good economical effect
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Embodiment 1
[0032] Step 1: Add 2-aminopyridine (0.5 mmol), methylpentanone (10.0 mmol), cuprous iodide (0.25 mmol) and boron trifluoride diethyl ether (0.14 mL) into 2 mL of DMF solvent under oxygen protection , reacted at 60°C for 12 hours; after the reaction, cooled to room temperature, extracted with ethyl acetate (30 mL), dried over anhydrous sodium sulfate, concentrated silica gel column chromatography (volume ratio of petroleum ether to ethyl acetate was 3 : 1) Purification to obtain 2-(2-pentyl)imidazo[1,2-a]pyridine.
[0033] Step 2: Add 2-(2-pentyl)imidazo[1,2-a]pyridine (0.20 mmol), phenylglyoxal hydrate (0.24 mmol) and xylene (2 mL) synthesized in step 1 Reaction occurred in the reaction flask; stirring was carried out at 80° C. for 6 hours in the presence of air; after the reaction, the reaction system was cooled to room temperature. After extraction with ethyl acetate, drying over anhydrous sodium sulfate, and purification by concentrated silica gel column chromatography (th...
Embodiment 2
[0042] Step 1: Add 2-aminopyridine (0.5 mmol), cyclopropylmethyl ketone (10.0 mmol), cuprous iodide (0.25 mmol) and boron trifluoride ether (0.14 mL) into 2 mL of DMF under oxygen protection solvent, reacted at 60°C for 12 hours; after the reaction, cooled to room temperature, extracted with ethyl acetate (30 mL), dried over anhydrous sodium sulfate, concentrated silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 4:1) purification to obtain 2-(2-(cyclopropane)imidazo[1,2-a]pyridine.
[0043] Step 2: Combine 2-(2-(cyclopropane)imidazo[1,2-a]pyridine (0.20 mmol), phenylglyoxal hydrate (0.24 mmol) and xylene (2 mL) synthesized in step 1 Add it into a reaction flask to react; Stir at 80°C for 6 hours in the presence of air; and ethyl acetate volume ratio of 4:1) to obtain the product 1-(2-cyclopropylimidazo[1,2-a]pyridin-3-yl)-2-phenylethane-1,2 - diketone.Reaction yield is 56%, and its structural formula is as follows:
[0044]
[004...
Embodiment 3
[0052] Step 1: Under oxygen protection, add 2-aminopyridine (0.5 mmol), acetophenone (10.0 mmol), cuprous iodide (0.25 mmol) and boron trifluoride ether (0.14 mL) into 2 mL of DMF solvent , reacted at 60°C for 12 hours; after the reaction, cooled to room temperature, extracted with ethyl acetate (30 mL), dried over anhydrous sodium sulfate, concentrated silica gel column chromatography (volume ratio of petroleum ether to ethyl acetate was 3: 1) Purification to obtain imidazo[1,2-a]-pyridine compound.
[0053] Step 2: Add imidazo[1,2-a]-pyridine (0.20 mmol), 3-methoxyphenylglyoxal hydrate (0.24 mmol) and xylene (2 mL) synthesized in step 1 into the reaction flask The reaction occurred in ; the mixture was stirred at 80° C. for 6 hours in the presence of air; after the reaction, the reaction system was cooled to room temperature. Extracted with ethyl acetate, dried over anhydrous sodium sulfate, and purified by concentrated silica gel column chromatography (the volume ratio of ...
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