Method for preparing polysubstituted 4,5-pyrazoline compound

Abstract

The invention discloses a method for preparing a polysubstituted 4,5-pyrazoline compound. The method comprises the following steps: adding a bivalent copper salt, neopentanoic acid, sulfur ylide and phenylsulfonyl hydrazone into an organic solvent, heating the temperature of the reactants to 100 DEG C to 110 DEG C for reaction, and carrying out aftertreatment after the reaction ends up, thereby obtaining the polysubstituted 4,5-pyrazoline compound. According to the method, the steps are simple, the raw materials are readily available, the reaction is not required to be carried out under anhydrous and oxygen-free conditions, and thus, the operation is facilitated. The reaction can be easily extended to a gram grade, and thus, the method has a large-scale application prospect.

Description

technical field

[0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of multi-substituted 4,5-dihydropyrazole compounds. Background technique

[0002] As an important five-membered nitrogen-containing heterocyclic ring, 4,5-dihydropyrazole compound is the core structure skeleton of many natural products with biological activity and organic functional molecules. It is used in medicine, biology, functional materials, dyes and pesticides, etc. fields have a wide range of uses (Journal of Medicinal Chemistry, 2009, 52(14), 4329-4337), and many 4,5-dihydropyrazole molecules have shown strong physiological activities, such as sedative pain relief, anti-inflammatory, Bactericidal, hypoglycemic and hypnotic activities, etc., and sulfonyl heterocyclic compounds are the key structures of many new drugs and pesticides:

[0003]

[0004] The main methods of synthesizing 4,5-dihydropyrazole in literature reports are: 1. using α, β unsa...

Examples

Embodiment Construction

[0035] The present invention will be further described below in conjunction with specific embodiments.

[0036] Add divalent copper salt, pivalic acid, sulfur ylide (II), benzenesulfonylhydrazone (III) and 3ml of organic solvent into a 35ml Schlenk tube according to the raw material ratio in Table 1, mix and stir evenly, and follow the reaction in Table 2 After the conditional reaction is completed, filter, mix the sample with silica gel, and separate and purify by column chromatography to obtain the corresponding 4,5-dihydropyrazole compound (I). The reaction process is shown in the following formula:

[0037]

[0038] Table 1

[0039]

[0040] Table 2

[0041]

[0042]

[0043] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Me is methyl, OMe is methoxy, Et is ethyl, t-Bu is tert-butyl, Ph is phenyl, DMSO is dimethyl base sulfoxide.

[0044] The structure confirmation data of the compounds prepared in Examples 1-8:

[0045] The ...

technical field

[0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of multi-substituted 4,5-dihydropyrazole compounds. Background technique

[0002] As an important five-membered nitrogen-containing heterocyclic ring, 4,5-dihydropyrazole compound is the core structure skeleton of many natural products with biological activity and organic functional molecules. It is used in medicine, biology, functional materials, dyes and pesticides, etc. fields have a wide range of uses (Journal of Medicinal Chemistry, 2009, 52(14), 4329-4337), and many 4,5-dihydropyrazole molecules have shown strong physiological activities, such as sedative pain relief, anti-inflammatory, Bactericidal, hypoglycemic and hypnotic activities, etc., and sulfonyl heterocyclic compounds are the key structures of many new drugs and pesticides:

[0003]

[0004] The main methods of synthesizing 4,5-dihydropyrazole in literature reports are: 1. using α, β unsa...

Examples

Embodiment Construction

[0035] The present invention will be further described below in conjunction with specific embodiments.

[0036] Add divalent copper salt, pivalic acid, sulfur ylide (II), benzenesulfonylhydrazone (III) and 3ml of organic solvent into a 35ml Schlenk tube according to the raw material ratio in Table 1, mix and stir evenly, and follow the reaction in Table 2 After the conditional reaction is completed, filter, mix the sample with silica gel, and separate and purify by column chromatography to obtain the corresponding 4,5-dihydropyrazole compound (I). The reaction process is shown in the following formula:

[0037]

[0038] Table 1

[0039]

[0040] Table 2

[0041]

[0042]

[0043] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Me is methyl, OMe is methoxy, Et is ethyl, t-Bu is tert-butyl, Ph is phenyl, DMSO is dimethyl base sulfoxide.

[0044] The structure confirmation data of the compounds prepared in Examples 1-8:

[0045] The ...

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