Preparation method of 3-trifluoromethyl substituted 1,2,4-triazole compound

A technology of trifluoromethyl and triazole, which is applied in the field of preparation of 1,2,4-triazole compounds, can solve the problems of not widely reported synthetic methods, and achieve strong designability, high reaction efficiency, and tolerance wide range of effects

Inactive Publication Date: 2021-08-27
HANGZHOU VOCATIONAL & TECHN COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Most of the synthetic methods that have been developed are all substituted 1,2,4-triazoles, and the synthetic methods of 3,4-disubstituted 1,2,4-triazoles are not widely reported.

Method used

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  • Preparation method of 3-trifluoromethyl substituted 1,2,4-triazole compound
  • Preparation method of 3-trifluoromethyl substituted 1,2,4-triazole compound
  • Preparation method of 3-trifluoromethyl substituted 1,2,4-triazole compound

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Embodiment Construction

[0032] The present invention will be further described below in conjunction with specific embodiments.

[0033] Add molybdenum hexacarbonyl, cuprous acetate, triethylamine, trifluoroethylimidoyl chloride (II), functionalized isonitrile (III) and 2 mL of organic solvent into a 35 mL Schlenk tube according to the raw material ratio in Table 1, and mix Stir evenly, react for 18-30 hours according to the reaction conditions in Table 2, filter, mix the sample with silica gel, and obtain the corresponding 3-trifluoromethyl-substituted 1,2,4-triazole compound (I) through column chromatography purification , the reaction process is shown in the following formula:

[0034]

[0035] The raw material addition of table 1 embodiment 1~15

[0036]

[0037] Table 2

[0038]

[0039]

[0040] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, Me is methyl, Et is ethyl, t-Bu is tert-butyl, OMe is methoxy, SMe is methylsulfide Base, NO 2...

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Abstract

The invention discloses a preparation method of a 3-trifluoromethyl substituted 1,2,4-triazole compound. The preparation method comprises the following steps: adding molybdenum hexacarbonyl, cuprous acetate, triethylamine, a molecular sieve, trifluoroethylimidoacyl chloride and functionalized isonitrile (NIITP) into an organic solvent, conducting reacting at 70-90 DEG C for 18-30 hours, and after the reaction is completed, performing post-treatment to obtain the 3-trifluoromethyl substituted 1,2,4-triazole compound. The preparation method has the advantages of mild conditions, simple operation, cheap and easily available initial raw materials and high reaction efficiency, can be expanded to gram-level reaction, can synthesize trifluoromethyl-containing 1,2,4-triazole compounds substituted by different functional groups through substrate design, and is convenient to operate and widened in applicability.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of 1,2,4-triazole compound substituted by 3-trifluoromethyl. Background technique [0002] 1,2,4-Triazole compound is an extremely important five-membered nitrogen-containing heterocyclic ring, which widely exists in molecular skeletons with biological and pharmaceutical activities (Chem. Rev. 2010, 110, 1809-1827). Many drugs contain 1,2,4-triazole molecular structure, such as deferasirox, maravirox and sitagliptin. Multi-substituted 1,2,4-triazole molecules are often used in ligand chemistry. Trifluoromethyl can significantly improve the physicochemical properties of the parent molecule, such as electronegativity, bioavailability, metabolic stability, and lipophilicity (J.Med.Chem.2015, 58, 8315-8359). Therefore, the construction of trifluoromethyl-substituted 1,2,4-triazole compounds has important theoretical research significance and practical applicati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08
CPCC07D249/08
Inventor 王慧陈铮凯
Owner HANGZHOU VOCATIONAL & TECHN COLLEGE
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