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Synthesis method of polysubstituted pyrazole compound

A synthesis method and compound technology, applied in the field of synthesis of multi-substituted pyrazole compounds, can solve the problems of unfriendly environment, uneconomical atoms, cumbersome operation, etc., achieve non-toxic and harmless solvents, increase the scope of application, and simple reaction conditions Effect

Active Publication Date: 2022-01-25
成都普康唯新生物科技有限公司
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to provide a synthetic method of multi-substituted pyrazole compounds, using cheap and easy-to-obtain commodities as raw materials, under the action of very cheap base catalysis and environmentally harmless solvents, only need to react at room temperature to simultaneously Constructed 1,3,4-trisubstituted and 1,3,4,5-tetrasubstituted multi-substituted pyrazole compounds; solved the problem of lengthy routes, uneconomical atoms, unfriendly environment, and operational difficulties in the synthesis of such compounds. cumbersome and other issues

Method used

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  • Synthesis method of polysubstituted pyrazole compound
  • Synthesis method of polysubstituted pyrazole compound
  • Synthesis method of polysubstituted pyrazole compound

Examples

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Embodiment 1

[0035] In this example, the compound 1,3,4-triphenyl-1H-pyrazole of the formula III-1 was prepared by using the compound N-phenylbenzohydrazone chloride of the formula I-1 and the compound cinnamaldehyde of the formula II-1 as standard substrates And formula IV-1 compound 1,3,5-triphenyl-1H-pyrazole-4-formaldehyde, its reaction formula is:

[0036]

[0037] The specific operation is: pre-dry the 10mL reaction tube and the magnetic stir bar, and then add 100mg N-phenylbenzohydrazone acid chloride (0.435mmol) and 150.2mg K 2 CO 3 (1.087mmol), then add 2.2mL ethanol solvent, finally add 69.00mg cinnamaldehyde (0.522mmol), the whole reaction is placed in normal temperature to react, TLC monitors the whole reaction process, after the reaction finishes, the solvent is concentrated, and the crude product obtained is used A mixture of petroleum ether and ethyl acetate (30 / 1, v / v) was used as the eluent, and 300-400 mesh silica gel was used as the separation resin for column chroma...

Embodiment 2

[0041] In this embodiment, the compound N-phenylbenzohydrazone chloride of formula I-1 and the compound cinnamaldehyde of formula II-1 are used as standard substrates to study the reaction conditions for the synthesis of base-catalyzed multi-substituted pyrazole compounds. The reaction formula for:

[0042]

[0043] Reaction conditions and results are shown in Table 1:

[0044] Table 1

[0045]

[0046] In Table 1, "equiv" means equivalent; temperature "rt" means room temperature; a means that 2.5 equivalents of DDQ have been added to the reaction system; b means anhydrous and oxygen-free conditions.

Embodiment 3

[0048] This embodiment discloses formula III-2 compound (4-bromophenyl)-1,3-diphenyl-1H-pyrazole and formula IV-2 compound 5-(4-bromophenyl)-3-(ring Preparation of hexa-1,3-dien-1-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde:

[0049]

[0050] The 10mL reaction tube and magnetic stirrer were pre-dried, and then 100mg N-phenylbenzohydrazone chloride (0.435mmol) and 150.2mg K 2 CO 3 (1.087mmol), then add 2.2mL ethanol solvent, finally add 110.17mg p-bromocinnamaldehyde (0.522mmol), the whole reaction is placed in normal temperature to react, TLC monitors the whole reaction process, after the reaction finishes, the solvent is concentrated, and the obtained crude The product uses a mixture of petroleum ether and ethyl acetate (30 / 1, v / v) as the eluent, and uses 300-400 mesh silica gel as the separation resin for column chromatography to obtain (4-bromophenyl)-1,3 -Diphenyl-1H-pyrazole (47.4 mg, light yellow oil) and 5-(4-bromophenyl)-3-(cyclohexa-1,3-dien-1-yl)-1-phenyl - 1H-pyra...

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Abstract

The invention discloses a synthesis method of a polysubstituted pyrazole compound, belongs to the technical field of organic synthesis, and solves the problems of lengthy route, uneconomical atoms, unfriendly environment and tedious operation in the synthesis process of the skeleton of the compound. According to the synthesis method of the polysubstituted pyrazole compound disclosed by the invention, a compound shown as a formula I and a compound shown as a formula II react under an alkaline condition to generate a compound shown as a formula III and a compound shown as a formula IV. In the invention, the 1,3,4-trisubstituted and 1,3,4,5-tetra-substituted polysubstituted pyrazole compounds can be simultaneously constructed by taking cheap and easily available commodities as raw materials and under the action of very cheap base catalysis and environment-harmless solvents only through normal-temperature reaction; for a synthetic product 1,3,4,5-tetra-substituted pyrazole compound, a 4-position aldehyde group can be subjected to structural modification, so that a target functional group is introduced, and the compound has different biological activities.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing polysubstituted pyrazole compounds. Background technique [0002] Pyrazoles are an important class of five-membered nitrogen-containing heterocyclic compounds, which widely exist in many natural products, bioactive molecules and drug molecules, and are an important class of organic synthesis intermediates. [0003] In the prior art, there are mainly two methods for the preparation of multi-substituted pyrazole compounds: one is to use the knorr pyrazole synthesis method, and the other is to modify the structure of pyrazole compounds through electrophilic or nucleophilic substitution reactions. For the former, the reaction catalyst is concentrated acid and the reaction temperature is relatively high, which has a greater conflict with production safety and green development. For the latter, due to the unique spatial structure and electronic effe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12C07D409/04
CPCC07D231/12C07D409/04Y02P20/55
Inventor 何永磊鲁军邓赟李美美黄辉任青
Owner 成都普康唯新生物科技有限公司
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