Compound with 3-(2-hydroxyphenyl) quinoline structural unit and preparation method and application thereof
A technology of hydroxyphenyl and structural units, which is applied in the field of compounds with 3-quinoline structural units, can solve the problems of narrow substrate range and achieve the effects of short reaction cycle, stable preparation and expanded raw materials
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Embodiment 1
[0024] Embodiment 1: optimization of conditions
[0025] Add dibenzo-1,4-oxazepine imine 1a (0.1 mmol), phenylacetylene 2a (0.2 mmol), iron salt (0.01-0.1 mmol) and re-distilled 1 mL of solvent in sequence in a sealed tube, After sealing, stir the reaction at 80-100°C. After the reaction, cool to room temperature, add dichloromethane (10mL) and water (10mL) to dilute, separate the layers, and continue to extract the water phase with dichloromethane ( 2 × 10mL), the organic phases were combined, and dried with anhydrous sodium sulfate. After removing the solvent, direct column chromatography (volume ratio, petroleum ether / ethyl acetate=3:1—1:1 elution) was separated to obtain a pure product, The reaction formula is as follows:
[0026]
[0027] Table 1. Preparation of 3-(2-hydroxyphenyl)quinoline 3aa: optimization of different reaction conditions
[0028]
[0029]
[0030] As can be seen from Table 1, the optimum reaction conditions are: the iron salt is FeCl 3 , th...
Embodiment 2
[0031] Example 2: Anhydrous ferric chloride promotes the reaction of dibenzo-1,4-oxazepine imine 1a with different alkynes 2a-2n to synthesize quinoline derivatives 3aa-3an
[0032] Add dibenzo1,4-oxazepine imine 1a (0.4mmol), terminal alkynes 2a-2n (0.8mmol), anhydrous ferric chloride (0.4mmol) and re-distilled 1 ml of 1,2-dichloroethane (DCE), sealed and stirred at 100°C for 10 hours. After the reaction was completed, cool to room temperature, add dichloromethane (10mL) and water (10mL) to dilute, separate layers after separation, continue to extract the aqueous phase with dichloromethane (2×10mL), combine the organic phases, and wash with anhydrous sulfuric acid Drying over sodium, removal of the solvent and direct column chromatography (petroleum ether / ethyl acetate) gave the pure product.
[0033] The reaction formula is as follows:
[0034]
[0035] Table 2. Preparation of quinoline derivatives 3aa-3an from the reaction of dibenzo1,4-oxazepine imine 1a with differen...
Embodiment 3
[0053] Example 3: Anhydrous ferric chloride promotes the reaction of different dibenzo 1,4-oxazepine imines 1b-1m and phenylacetylene 2a to synthesize quinoline derivatives 3ba-3ma
[0054] In a sealed tube, add differently substituted dibenzo-1,4-oxazepine imines 1b-1m (0.4mmol), phenylacetylene 2a (0.8mmol), anhydrous ferric chloride (0.4mmol) and re- Distilled 1 ml of 1,2-dichloroethane (DCE), sealed and stirred at 100°C for 10 hours. After the reaction was completed, cool to room temperature, add dichloromethane (10mL) and water (10mL) to dilute, separate the layers, and continue to extract the aqueous phase with dichloromethane (2×10mL), combine the organic phases, and wash with anhydrous sulfuric acid Sodium drying, after removing the solvent, direct column chromatography (petroleum ether / ethyl acetate elution) separates and obtains pure product, and reaction formula is as follows:
[0055]
[0056] The obtained quinoline product characterization data are as follows:...
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