Method for synthesizing quinoline and quinazoline compounds through cobalt catalysis

A technology of quinazolines and compounds, which is applied in the field of organic synthesis, can solve problems such as limiting industrial application prospects, and achieve the effects of low cost, high catalytic activity, and good application prospects

Pending Publication Date: 2021-12-31
HEBEI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] It can be seen from these existing technologies that although the non-acceptor dehydrogenation coupling catalytic system can more efficiently catalyze the synthesis of quinoline and quinazoline compounds, most of the catalytic systems are noble metal catalysts, that is to say, they need to be passed through The preparation of metal complexes by means of organic synthesis, or the use of organic phosphine compounds sensitive to air and humidity as ligands, these aspects limit its industrial application prospects

Method used

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  • Method for synthesizing quinoline and quinazoline compounds through cobalt catalysis
  • Method for synthesizing quinoline and quinazoline compounds through cobalt catalysis
  • Method for synthesizing quinoline and quinazoline compounds through cobalt catalysis

Examples

Experimental program
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Effect test

Embodiment 1

[0049] 2-aminobenzyl alcohol 1a (123.2 mg, 1.0 mmol), acetophenone 2a (120.2 mg, 1.0 mmol), Co(OAc) were added to the reaction vessel 2 4H 2 O (19.9 mg, 0.08 mmol) and KO t Bu (112.0 mg, 1.0 mmol). Under an argon atmosphere, 2 mL of toluene was added and heated at 110 °C for 12 h. After cooling to room temperature, 10 mL of water was added, and the mixture was extracted with EtOAc (3×10 mL). The combined organic phases were concentrated under reduced pressure. The residue was then purified by flash column chromatography (petroleum ether:ethyl acetate 100:1, v / v) to give 3a (198.9 mg, yield 97%) as a white solid, whose NMR spectrum was shown in figure 1 shown.

Embodiment 2

[0051] 2-aminobenzyl alcohol 1a (123.2 mg, 1.0 mmol), acetophenone 2a (120.2 mg, 1.0 mmol), Co(OAc) were added to the reaction vessel 2 • 4H 2 O (19.9 mg, 0.08 mmol) and KO t Bu (78.4 mg, 0.7 mmol). Under an argon atmosphere, 2 mL of toluene was added and heated at 110 °C for 12 h. After cooling to room temperature, 10 mL of water was added, and the mixture was extracted with EtOAc (3×10 mL). The combined organic phases were concentrated under reduced pressure. The residue was then purified by flash column chromatography (petroleum ether:ethyl acetate 100:1, v / v) to obtain white solid 3a (168.2 mg, yield 82%).

Embodiment 3

[0053] 2-aminobenzyl alcohol 1a (123.2 mg, 1.0 mmol), acetophenone 2a (144.2 mg, 1.2 mmol), Co(OAc) were added to the reaction vessel 2 • 4H 2 O (24.9 mg, 0.1 mmol) and KO t Bu (112.0 mg, 1.0 mmol). Under an argon atmosphere, 2 mL of toluene was added and heated at 110 °C for 12 h. After cooling to room temperature, 10 mL of water was added, and the mixture was extracted with EtOAc (3×10 mL). The combined organic phases were concentrated under reduced pressure. The residue was then purified by flash column chromatography (petroleum ether:ethyl acetate 100:1, v / v) to obtain white solid 3a (196.9 mg, yield 96%).

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Abstract

The invention discloses a method for synthesizing quinoline and quinazoline compounds through cobalt catalysis, benzene compounds with amino groups and hydroxyl groups and ketone compounds or cyanophenyl compounds are used as raw materials, the quinoline or quinazoline compounds are obtained through a receptor-free dehydrogenation coupling reaction in the presence of a catalyst and alkali, and the catalyst is cobalt acetate. According to the method, the acceptor-free dehydrogenation coupling reaction is efficiently catalyzed by directly using the cobalt acetate as the catalyst, metal cobalt does not need to be prepared into a corresponding metal complex, a ligand does not need to be used, the operation is simple, and the cost is low. The reaction system can catalyze synthesis of various quinoline and quinazoline compounds, the catalytic reaction has good functional group compatibility and high catalytic activity, products with high yield can be obtained, the reaction conditions are mild, and the method has good application prospects.

Description

technical field [0001] The invention relates to a synthesis method of quinazoline and its derivatives or quinoline and its derivatives, in particular to a method that uses cobalt acetate as a catalyst, does not need to use ligands, has mild reaction conditions, good environmental protection, simple operation and low cost. The invention relates to a synthesis method of quinazoline and its derivatives or quinoline and its derivatives with low reaction yield and high reaction yield, belonging to the technical field of organic synthesis. Background technique [0002] Nitrogen heterocyclic compounds have good pharmaceutical and biological activities. As an important constituent skeleton of most drug molecules and natural products, developing and designing efficient and green synthetic methodologies for the preparation of nitrogen heterocyclic compounds has always been one of the hot areas of chemical research. . [0003] Quinoline and its derivatives are an important class of ni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/78
CPCC07D239/78
Inventor 林进马宗文郝志强
Owner HEBEI NORMAL UNIV
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