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Method for preparing multi-substituted quinoline aromatic ring pyridine derivatives

A technology of cyclization and compounds, applied in the field of chemistry, can solve environmental problems such as unfriendly, achieve high atom utilization, high chemical selectivity, and simple separation process

Active Publication Date: 2016-03-30
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these synthetic methods also have different disadvantages, some produce halogen-containing waste, some use some strong acid conditions, and there are reagents that are not friendly to the environment, etc.

Method used

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  • Method for preparing multi-substituted quinoline aromatic ring pyridine derivatives
  • Method for preparing multi-substituted quinoline aromatic ring pyridine derivatives
  • Method for preparing multi-substituted quinoline aromatic ring pyridine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Weigh successively 0.0891g of compound toluene (0.5mmol) belonging to formula III, 0.2191g of phenyl-1H-tetrazole (1.5mmol) belonging to formula II, 0.0031g [Cp*RhCl 2 ] 2 (0.005mmol), 0.1997gCu(OAc) 2 ·H 2 O (1.0mmol) and 0.0984g potassium acetate (1.0mmol) were placed in a 25mL sealed tube containing a magnetic stirrer, and 2.0mL N,N-diethylformamide was added. Seal the sealed tube under nitrogen, put it into an oil bath at 120° C. and stir for 6 hours. After the reaction, column separation was carried out using petroleum ether-ethyl acetate as eluent to obtain 0.1007 g of white solid, and the isolated yield of the target product 2-amino-3,4-diphenylquinoline was 68%.

[0046] figure 1 and figure 2 The proton nuclear magnetic resonance spectrum and carbon spectrum of the product prepared in this embodiment are respectively, as can be seen from the figure, the structure of the compound is correct.

Embodiment 2

[0048] Weigh successively 0.0891g toluene (0.5mmol), 0.2401g p-methylphenyl-1H-tetrazole (1.5mmol), 0.0031g [Cp*RhCl 2 ] 2 (0.005mmol), 0.1997gCu(OAc) 2 ·H 2 O (1.0mmol) and 0.0984g potassium acetate (1.0mmol) were placed in a 25mL sealed tube containing a magnetic stirrer, and 2.0mL N,N-diethylformamide was added. Seal the sealed tube under nitrogen, put it into an oil bath at 120° C. and stir for 6 hours. Carry out column separation with sherwood oil-ethyl acetate as eluent after reaction finishes, obtain white solid 0.1072g, the isolated yield of target product 6-methyl-2-amino-3,4-diphenylquinoline is 69%.

Embodiment 3

[0050] Weigh successively 0.0891g toluene (0.5mmol), 0.2624g p-ethylphenyl-1H-tetrazole (1.5mmol), 0.0031g [Cp*RhCl 2 ] 2 (0.005mmol), 0.1997gCu(OAc) 2 ·H 2 O (1.0mmol) and 0.0984g potassium acetate (1.0mmol) were placed in a 25mL sealed tube containing a magnetic stirrer, and 2.0mL N,N-diethylformamide was added. Seal the sealed tube under nitrogen, put it into an oil bath at 120° C. and stir for 6 hours. After the reaction, use petroleum ether-ethyl acetate as eluent to carry out column separation to obtain 0.1215 g of white solid, and the isolated yield of the target product 6-ethyl 2-amino-3,4-diphenylquinoline is 75 %.

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Abstract

The invention discloses a method for preparing multi-substituted quinoline-type aromatic ring pyridine derivatives. The method comprises the steps of mixing phenyl tetrazole compounds represented by a formula II, an alkyne compound represented by a formula III, alkali, an oxidizing agent and a catalyst well, carrying out cyclization-denitrification cascade reaction to obtain the compound represented by the formula I after the reaction is completed. The method has the following characteristics that: (1) the method is economic; (2) the method is convenient; the final product can be obtained only by virtue of one step, feeding once and separating once in the reaction, since the reaction has high chemical selectivity, so that the separation process is also very simple. (3) the method is universal; and (4) the method is green. The prepared product is obtained by releasing one part of nitrogen from the obtained reaction intermediate, and since no other waste gases are discharged, so that no environmental pollution is caused. More importantly, the azacyano aniline as a byproduct of the reaction can be used as a new chemical raw material to be involved in other reactions. The reaction has the advantages of higher utilization of atoms and no environmental pollution.

Description

technical field [0001] The invention belongs to the field of chemistry, and relates to the catalytic synthesis of fine chemical products, in particular to a method for preparing polysubstituted quinoline aromatic ring pyridine derivatives. Background technique [0002] Quinoline and its derivatives are a common class of heterocyclic compounds with pharmacological and biological activities, which widely exist in nature. Many quinoline alkaloids are used as medicines due to their outstanding biological activity. For example, the alkaloid cinchona alkaloid extracted from the bark of the cina bark, also known as quinine, has a good anti-disease effect; The camptothecin extracted from the tree is also a kind of heterocyclic compound containing quinoline ring with anticancer effect. Many biologically active alkaloids, such as pilocarpines, piperines and vanillinines, also contain quinoline skeletons (Michael, J.P., Nat. Prod. Rep., 2001, 18, 543). [0003] Due to their unique ph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/38
CPCC07D215/38
Inventor 华瑞茂张磊
Owner TSINGHUA UNIV