Preparation method of pyrazolo[1,5-a]pyridine derivative

A derivative, 5-a technology, applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, limited range of substrates, toxic oxidants, etc., and achieve the effect of simple method, high yield and mild conditions

Active Publication Date: 2021-04-20
GUIZHOU MINZU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The present invention aims to solve the problem that the existing synthetic method of pyrazolo[1,5-a]pyridine structure requires metal catalysis, limited range of substrates, low overall yield of multi-step reactions, stoichiometric additives, toxic oxidants, and oxygen-free Technology, harsh reaction conditions, and provide a kind of preparation method of pyrazolo[1,5-a]pyridine derivatives

Method used

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  • Preparation method of pyrazolo[1,5-a]pyridine derivative

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specific Embodiment approach 1

[0016]BEST MODE FOR CARRYING OUT THE INVENTION First: The preparation method of pyrazole and [1,5-a] pyridine derivative is carried out in the following steps:

[0017]At room temperature, pyridine, unsaturated, 2,3-dichloro-5,6-dicanoquinone was dissolved in an organic solvent, with a drop of 5 ml / min ~ 6 ml / min, and three B The amine is at a temperature of from 0 ° C to 10 ° C and the stirring speed of 200 r / min to 400r / min, and the solvent is concentrated by the rotary evaporator, and purified by silica gel column chromatography. And [1,5-a] pyridine derivative;

[0018]The structural form of the pyridine salt isR1Alkyl, alkoxy, halogen, trifluoromethyl or phenyl, aromatic ring Ar is pyridine, quinoline, pyridine derivative or quinoline derivative;

[0019]The structural general formula of the unsaturatedR2Hydrogen, alkyl or aryl, R3Cyano, ester, ketone or aldehyde, x is bromine or chlorine;

[0020]The molar ratio of the pyridine salt and the unsaturated olefin is 1: (1.5 to 2); the...

specific Embodiment approach 2

[0027]DETAILED DESCRIPTION OF THE INVENTION The present embodiment is different from that of the particular embodiment: the organic solvent is acetonitrile, toluene, N, N-dimethylformamide or dimethyl sulfoxide. Other as the specific embodiment.

specific Embodiment approach 3

[0028]DETAILED DESCRIPTION OF THE INVENTION 3: The present embodiment is different from that of the specific embodiment one or two: the solvent used by the silica gel column chromatography is a mixed solvent for petroleum ether and ethyl acetate. Others are the same as those of the specific embodiments.

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Abstract

The invention discloses a preparation method of pyrazolo[1,5-a]pyridine derivatives, and belongs to the field of organic synthesis. The problems that an existing pyrazolo[1,5-a]pyridine structure synthesis method needs metal catalysis, the substrate range is limited, the total yield of multi-step reaction is low, stoichiometric additives, toxic oxidants and oxygen-free technologies are adopted, and reaction conditions are harsh are solved. The method comprises the steps: dissolving pyridinium salt, unsaturated alkene and 2,3-dichloro-5,6-dicyanobenzoquinone in an organic solvent, dropwise adding triethylamine to react, concentrating by a rotary evaporator to remove the solvent, and separating and purifying by silica gel column chromatography to obtain the pyrazolo[1,5-a]pyridine derivative.

Description

Technical field[0001]The present invention belongs to the field of organic synthesis.Background technique[0002]Pyrazole [1,5-A] pyridine core skeleton structure is thereby having special biological and chemical properties thereby in the fields of natural products, pesticides, pharmaceuticals (compounds 1 and 2), catalysts (Compound 3) and functional materials. It is important to apply value. At the same time, the pyrazole [1,5-a] pyridine compound is widely distributed in nature, the number, the type of structure is rich, and the biological activity is significant and diversified. It has attracted attention in the field of medical research and development, and has been successful. The clinical application of success, the market The demand is huge, the synthetic research significance is significant.[0003]Pyrazole and [1,5-A] pyridine active compound are widely distributed among natural products and drug molecules, are common organic molecular blocks. Pyrazole and [1,5-A] pyridine cor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCY02A50/30
Inventor 王俊雷蔡小华罗迎春文竹
Owner GUIZHOU MINZU UNIV
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