阅读说明：本技术 一种1h-氮杂环丙烯类化合物及其合成方法 (1H-aziridine compound and synthesis method thereof ) 是由 尹光伟 李方怿 刘岩 张娜 张海文 李正 于 2019-09-04 设计创作，主要内容包括：一种1H-氮杂环丙烯类化合物及其合成方法,其特征在于：由结构通式II<Image he="144" wi="276" file="DDA0002191181450000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>在催化剂和氧化剂的作用下,合成得到结构通式I<Image he="231" wi="304" file="DDA0002191181450000012.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>其中R<Sup>1</Sup>基团为脂肪基或者芳香环或者为芳香取代基,R<Sup>2</Sup>基团为脂肪基、芳香基或取代芳香基。本方法制备方法操作简单,反应条件温和、原料简单易得,反应步骤少,转化率和反应收率高,官能团兼容性好,底物适用范围广。(A1H-aziridine compound and a synthesis method thereof are characterized in that: is represented by the general formula II Under the action of catalyst and oxidant, the compound is synthesized to obtain the structural general formula I Wherein R is 1 The radical being an aliphatic or aromatic ring or an aromatic substituent, R 2 The group is aliphatic group, aromatic group or substituted aromatic group. The preparation method has the advantages of simple operation, mild reaction conditions, simple and easily obtained raw materials, few reaction steps, high conversion rate and reaction yield, good functional group compatibility and wide substrate application range.)

1. A1H-aziridine compound, characterized in that: the general structural formula I is as follows:

wherein R is¹The radical being an aliphatic or aromatic ring or an aromatic substituent, R²The group is aliphatic group, aromatic group or substituted aromatic group.

2. According to the claimsThe 1H-aziridine compound of claim 1, which is characterized in that: the structural general formula I is synthesized by a structural general formula II under the action of a catalyst and an oxidant, wherein the structural general formula II is as follows:Wherein R is¹The radical being an aliphatic or aromatic ring or an aromatic substituent, R²the group is aliphatic group, aromatic group or substituted aromatic group.

3. A 1H-aziridine compound according to claim 1, characterised in that: the catalyst is a copper salt transition metal catalyst.

4. A 1H-aziridine compound according to claim 3, characterised in that: the catalyst is copper trifluoromethanesulfonate or copper trifluoroacetate.

5. A 1H-aziridine compound according to claim 1, characterised in that: the oxidant is persulfate oxidant.

6. The 1H-aziridine compound according to claim 5, which is characterized by: the oxidant is potassium persulfate, sodium persulfate or ammonium persulfate.

7. A 1H-aziridine compound according to claim 1, characterised in that: the solvent is acetonitrile or nitromethane or dichloroethane or tetrahydrofuran.

8. A 1H-aziridine compound as claimed in any of claims 1 to 7, characterised in that: r1 is p-chlorophenyl, p-methoxyphenyl, p-fluorophenyl, o-methylphenyl, o-bromophenyl, 3, 4-dimethoxyphenyl, 2-thienyl, cyclopropyl, methoxy, furyl, trifluoromethyl, phenyl, R2 is methyl or phenyl.

9. A method for synthesizing 1H-aziridine compounds according to any of claims 1 to 7, characterised in that a substrate of general structural formula II is added with a catalyst, an oxidant and an organic solvent, and heated at 30-80 ℃ for 2-5 hours, wherein the molar ratio of general structural formula II to the catalyst to the oxidant is 1: 0.05: 0.5; the catalyst is copper trifluoromethanesulfonate or copper trifluoroacetate, the oxidant is potassium persulfate or sodium persulfate or ammonium persulfate, and the solvent is acetonitrile or nitromethane or dichloroethane or tetrahydrofuran.

Technical Field

The invention belongs to the field of organic synthesis methodologies, and relates to synthesis of a nitrogen-containing heterocyclic compound 1H-aziridine compound.

Background

The nitrogen-containing heterocyclic compound is an important branch of the heterocyclic compound as an intermediate of medicines, pesticides, dyes and other fine chemical products, and the application of the nitrogen-containing heterocyclic compound and derivatives thereof is more and more emphasized. Among them, nitrogen-containing tricyclic compounds, aziridine (aziridine) and aziridine compounds have been widely noticed as synthetic methods due to their high reactivity and diverse reactions. At present, the synthesis literature of 2H-aziridine compounds has been reported, and the synthesis of 1H-aziridine compounds has not been found.

Disclosure of Invention

In view of the above problems, an object of the present invention is to provide a method for synthesizing a 1H-aziridine compound. The preparation method has the advantages of simple operation, mild reaction conditions, simple and easily obtained raw materials, few reaction steps, high conversion rate and reaction yield, good functional group compatibility and wide substrate application range.

The technical scheme adopted by the invention for solving the technical problems is as follows: A1H-aziridine compound, characterized in that: the general structural formula I is as follows:

Wherein R is¹The radical being an aliphatic or aromatic ring or an aromatic substituent, R²The group is aliphatic group, aromatic group or substituted aromatic group.

The structural general formula I is synthesized by a structural general formula II under the action of a catalyst and an oxidant, wherein the structural general formula II is as follows:Wherein R is¹The radical being an aliphatic or aromatic ring or an aromatic substituent, R²The group is aliphatic group, aromatic group or substituted aromatic group.

The catalyst is a copper salt transition metal catalyst, preferably copper trifluoromethanesulfonate or copper trifluoroacetate.

The oxidant is persulfate oxidant, preferably potassium persulfate, sodium persulfate or ammonium persulfate.

The solvent is acetonitrile or nitromethane or dichloroethane or tetrahydrofuran.

A method for synthesizing a 1H-aziridine compound is characterized in that a general structural formula II is used as a substrate, a catalyst, an oxidant and an organic solvent are added, and the mixture is heated at 30-80 ℃ for 2-5 hours, wherein the molar ratio of the general structural formula II to the catalyst to the oxidant is 1: 0.05: 0.5; the catalyst is copper trifluoromethanesulfonate or copper trifluoroacetate, the oxidant is potassium persulfate or sodium persulfate or ammonium persulfate, and the solvent is acetonitrile or nitromethane or dichloroethane or tetrahydrofuran.

The invention has the advantages that:

The preparation method has the advantages of simple operation, mild reaction conditions, simple and easily obtained raw materials, few reaction steps, high conversion rate and reaction yield, good functional group compatibility and wide substrate application range.

Detailed Description

The technical solutions of the present invention will be described clearly and completely below, and it should be apparent that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.