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Preparation method of 1,3,5-trisubstituted 1,2,4-triazole compound

A compound and triazole technology, which is applied in the field of preparation of 1,2,4-triazole compounds, can solve the problems of poor regioselectivity and narrow substrate breadth, and achieves easy operation, convenient post-processing and practicality. strong effect

Active Publication Date: 2016-06-08
东营睿港招商服务有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, most of the methods described above have some limitations, such as the need for multiple synthetic steps to prefunctionalize the substrate, poor regioselectivity, and narrow substrate breadth, etc.

Method used

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  • Preparation method of 1,3,5-trisubstituted 1,2,4-triazole compound
  • Preparation method of 1,3,5-trisubstituted 1,2,4-triazole compound
  • Preparation method of 1,3,5-trisubstituted 1,2,4-triazole compound

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Embodiment 1～15

[0040] Add elemental iodine, tert-butanol peroxide (TBHP, 70% aqueous solution), hydrazone (II), aliphatic amine (III) and organic solvent 1mL in the Schlenk tube of 35mL according to the raw material ratio of Table 1, mix and stir evenly, After the reaction is completed according to the reaction conditions in Table 2, filter, mix the sample with silica gel, and obtain the corresponding 1,3,5-trisubstituted 1,2,4-triazole compound (I) through column chromatography purification, the reaction process is as follows The formula shows:

[0041]

[0042] The raw material addition of table 1 embodiment 1~11

[0043]

[0044]

[0045] Table 2

[0046]

[0047] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, OMe is methoxy, and n-Bu is n-butyl.

[0048] The structure confirmation data of some compounds:

[0049] The nuclear magnetic resonance (NMR) of the 1,2,4-triazole compound (I-1) prepared by embodiment 1 1 HNMR and 13 C...

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Abstract

The invention discloses a preparation method of a 1,3,5-trisubstituted 1,2,4-triazole compound. The preparation method comprises the following steps that simple substance iodine, tert-butyl hydroperoxide (a 70% aqueous solution), hydrazone and fatty amine are added into organic solvent, the materials are heated to the temperature of 80 DEG C-100 DEG C for a reaction, and after the reaction is complete, aftertreatment is performed to obtain the 1,3,5-trisubstituted 1,2,4-triazole compound. The preparation method has the advantages that the steps are simple, the raw materials are cheap and easy to obtain, and the reaction does not need to be performed under water-free and oxygen-free conditions; in addition, heavy metal does not need to be used as a catalyst, diversely substituted 1,2,4-triazole compounds with different substituted positions can be synthesized through the design, and the applicability of the method is widened while operation is convenient.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of a 1,3,5-trisubstituted 1,2,4-triazole compound. Background technique [0002] 1,2,4-Triazole compound, as an important nitrogen-containing five-membered heterocyclic ring, widely exists in various molecular structures with biological activity (Chem.Rev.2010,110,1809-1827), many drugs and The material molecules all contain the skeleton of the 1,2,4-triazole structure, such as the nitrogen-1-aryl substituted 1,2,4-triazole derivative ICL670 (deferasirox) as an active Iron complexing agents can be effectively used in the treatment of iron overload in vivo; in addition, 1,2,4-triazole derivatives containing pyridine rings can be used as potential inhibitors of cytochrome P450 isoenzymes, which have been successfully Among the chemotherapeutic drugs used to prevent and treat breast cancer: [0003] [0004] 1,2,4-Triazole molecules can also be used in meta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08
CPCC07D249/08
Inventor 陈铮凯李红礼任红军
Owner 东营睿港招商服务有限责任公司
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