Synthesis method of polysubstituted pyridine derivative

A synthesis method and derivative technology, applied in the field of synthesis of multi-substituted pyridine derivatives, to achieve the effects of easy operation, avoiding the use of transition metal catalysts and toxic ligands, and mild conditions

Inactive Publication Date: 2018-04-24
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, carbon dioxide fixation chemistry has been vigorously developed, but there is no public report on the activation of C=N to promote the breakage of C=N bonds and then the reconstruction of C=N bonds to form pyridine heterocycles.

Method used

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  • Synthesis method of polysubstituted pyridine derivative
  • Synthesis method of polysubstituted pyridine derivative
  • Synthesis method of polysubstituted pyridine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-9

[0033] Under a carbon dioxide atmosphere, add 0.2 mmol of asymmetrically substituted 1,3-butadiyne, 0.2 mmol of cesium carbonate, 0.6 mmol of DBU, a small amount of water and 2 mL of acetonitrile into the Schlenk reaction tube in sequence, and heat and stir in IKA for 24 hours. . After the reaction, cool to room temperature, transfer the reaction solution with 20 mL of ethyl acetate, prepare samples by rotary evaporation under reduced pressure, and separate by column chromatography to obtain the target products 4a-i and 5a-i.

[0034]

[0035]

[0036] In Examples 1-9, the reactions of various 1,4-diphenylbutadiynes substituted by different substituents at the para-position of the benzene ring and DBU were studied. According to the above experiments, it can be found that the reaction has wide substrate adaptability to the substituents such as alkyl, methoxy, ethoxy, fluoro, and chloro of the benzene ring, and the corresponding target product is obtained in a higher yield...

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Abstract

The invention discloses a synthesis method of a polysubstituted pyridine derivative and belongs to the technical field of organic chemistry. DBU and asymmetrically substituted 1,3-butadiyne are used as reaction materials to be subjected to a heating reaction to produce a polysubstituted pyridine compound with cesium carbonate as base in an acetonitrile solvent under the catalysis of CO2. CO2 activation is used to promote C=N bond breakage, the method is simple and convenient and adopts mild conditions, the functional polysubstituted pyridine compound is directly constructed, and the synthesismethod of pyridine heterocycles is broadened.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing polysubstituted pyridine derivatives. Background technique [0002] As an important nitrogen-containing heterocycle, pyridine exists in a variety of important compounds, including azine, vitamin niacin, and pyridoxine. It is not only the precursor of agricultural chemicals and drugs, but also an important dyeing aid and denaturant. Pyridine derivatives are often part of biomolecules, such as pyridine nucleotides and alkaloids. [0003] The synthesis of pyridine is usually divided into two steps: 1. breaking of the C=N bond of the raw material; 2. rebuilding of the C=N bond to synthesize the pyridine ring. Traditional C=N bond breaking is to use transition metal M, such as palladium, nickel, copper, cobalt, rhodium and other catalysts to catalyze the breaking of C=N bonds to form C-M and N-M or C-M-N substances. However, most transition metal...

Claims

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Application Information

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IPC IPC(8): C07D401/06C07D409/14
CPCC07D401/06C07D409/14
Inventor 刘建明岳园园闫旭洋赵淑芳
Owner HENAN NORMAL UNIV
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