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Method for synthesizing 3-cyanometidine [1, 5-a] quinoline compound

A technology of cyanoimidazole and synthesis method, applied in directions such as organic chemistry, can solve problems such as complicated operation, low total yield, limited structure-activity relationship and the like

Inactive Publication Date: 2018-09-14
ANHUI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few studies on the synthesis of cyano-substituted imidazo[1,5-a]pyridines. Patents US 20110021521 A1 and WO 2011149921 A1 disclose the synthesis of cyano-substituted imidazo[1,5-a]pyridines, which need to be synthesized first Imidazo[1,5-a]pyridine core, and then multi-step reaction to prepare cyano-substituted imidazo[1,5-a]pyridine, which has the characteristics of cumbersome operation and low overall yield
However, there is no report on the synthesis of 3-cyanoimidazo[1,5-a]quinolines, which limits the subsequent study of structure-activity relationships.

Method used

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  • Method for synthesizing 3-cyanometidine [1, 5-a] quinoline compound
  • Method for synthesizing 3-cyanometidine [1, 5-a] quinoline compound
  • Method for synthesizing 3-cyanometidine [1, 5-a] quinoline compound

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Embodiment 1-12

[0012] According to the raw material ratio and reaction conditions in Table 1 and Table 2, copper sulfate was first added to a 20mL dry three-port reaction tube, and after vacuuming and replacing oxygen three times, 2-methylquinoline compound (II) and aliphatic amine were added in sequence Compound (III), cyano source (IV) and 1-methyl-2-pyrrolidone were mixed and stirred evenly at room temperature, and under an oxygen atmosphere, after the reaction was completed according to the reaction conditions in Table 2, the reaction solution was cooled to room temperature, and the reaction Liquid was transferred to a separatory funnel, 30 ml of water was added to the separatory funnel, extracted with ethyl acetate (3×10 mL), dried over anhydrous sodium sulfate, and separated by silica gel column chromatography (eluent was ethyl acetate The mixed solution with petroleum ether, the volume ratio of the two is 1:4~8), to obtain the corresponding 3-cyanoimidazo[1,5-a]quinoline compound (I), ...

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Abstract

The invention belongs to the field of organic synthesis, and discloses a method for synthesizing 3-cyanometidine, which includes the following steps of: under the condition of temperature of 130 DEG Cand oxygen environment, by using copper sulfate as a catalyst, 2-methyl quinoline compound, aliphatic amine compound and organic cyanogens anion perform three-group series reaction in a solvent. After the reaction is finished, separation and purification are carried out to obtain imidazo [1, 5-a] quinoline compound with third bit replaced by a cyanogroup. The method has the advantages of simple and convenient operation, cheap and easily available raw materials, wide application range of the substrate, high yield and the like, and has wide application prospect in the fields of biological medicine, pesticide and optical materials.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a R 1 Substituted 2-methylquinoline compounds, R 2 Substituted aliphatic amine compounds with R 3 The substituted organic cyano source, under the catalysis of copper sulfate, regioselectively undergoes a three-component series reaction for the preparation of 3-cyano substituted imidazo[1,5-a]quinoline compounds. Background technique [0002] Imidazo[1,5-a]quinolines are a class of nitrogen-containing heterocyclic compounds that are widely used in the fields of biomedicine, pesticides and optical materials. The introduction of various functional groups at the 3-position of imidazo[1,5-a]quinoline compounds can have a significant impact on their physical, chemical and biological properties, thereby improving their application performance. Therefore, the synthesis of imidazo[1,5-a]quinoline compounds containing various functional groups by functionalizing the 3-position of imidaz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 魏红娟冯承涛李敬陈小平
Owner ANHUI UNIV OF SCI & TECH