A kind of 2-aryl-3-acylaminoquinoline derivative and preparation method thereof
A technology of amidoquinoline and derivatives, which is applied in the field of 2-aryl-3-amidoquinoline derivatives and their preparation, and achieves the effects of simple steps and mild reaction conditions
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[0042] The preparation method of described 2-aryl-3-amidoquinoline derivatives, comprises the following steps:
[0043] Using 2-Boc-aminobenzaldehyde as raw material, it undergoes condensation reaction with substituted acetophenone under alkaline conditions to obtain chalcone derivatives, and then cyclizes substituted cyclopropylamines through amination reagents, and the resulting products react with acid chlorides Reaction, and finally under acidic conditions, the deprotection and ring formation of the amino group occur simultaneously to obtain 2-aryl-3-amidoquinoline derivatives.
[0044] The method for preparing 2-aryl-3-amidoquinoline derivatives provided by the application, the specific reaction process is as follows:
[0045]
[0046] The preparation method of the 2-aryl-3-acylaminoquinoline derivatives provided by the application adopts a one-pot method, and the cyclopropylamine intermediate is directly in an acidic aqueous solution, and at the same time of deprotectio...
Embodiment 1
[0073] At room temperature, dissolve 0.442 g (2 mmol) of 2-Boc-aminobenzaldehyde in 10 ml of absolute ethanol solution, stir and add 0.322 g (2.4 mmol) of 4-methylacetophenone, and then slowly drop in an appropriate amount of Sodium hydroxide (mass concentration: 15%, 10mL) solution, continue to react at room temperature for 1 hour after the dropwise addition, and monitor the progress of the reaction by lc-ms. After the reaction is completed, pour it into 60 ml of ice water; after stirring, suction filter to obtain Char Ketone intermediate 0.642g, vacuum-dried for 8 hours, then take 0.337g (1mmol) of the above-mentioned chalcone intermediate and add it to 5 ml of acetonitrile solution, add 0.254g (1mmol) iodine, after a period of reaction, add 0.139g hydrochloric acid Hydroxylamine and 0.08g sodium hydroxide solid were stirred at room temperature until the reaction was completed, then slowly poured into 20 ml of ice water, extracted with dichloromethane, dried, suction filtered...
Embodiment 2
[0077] At room temperature, dissolve 0.442 g (2 mmol) of 2-Boc-aminobenzaldehyde in 10 ml of absolute ethanol solution, stir and add 0.36 g (2.4 mmol) of 4-methoxyacetophenone, and then slowly drop in an appropriate amount of Sodium hydroxide (mass concentration: 15%, 12mL) solution, continued to react at room temperature for 2 hours after dropping, and the reaction was monitored by lc-ms. After the reaction was completed, it was poured into 60 ml of ice water; Chalcone intermediate 0.671g, vacuum-dried for 10 hours, then take the above-mentioned chalcone intermediate 0.353g (1mmol) and join in 5 ml of acetonitrile solution, add 0.254g (1mmol) iodine, after a period of reaction, add 0.139g Hydroxylamine hydrochloride and 0.08g sodium hydroxide solid were stirred at room temperature until the reaction was completed, then slowly poured into 20 ml of ice water, extracted with dichloromethane, dried, suction filtered, concentrated, and recrystallized to obtain the cyclopropylamine ...
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