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

A compound, triazole technology, applied in the field of preparation of 1,2,4-triazole compound, achieves the effects of strong practicability, convenient post-processing, and strong designability

Active Publication Date: 2021-07-13
ZHEJIANG SCI-TECH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Nowadays, various methods for synthesizing 3,4,5-trisubstituted 1,2,4-triazoles have been reported in the literature, and the non-metal-promoted synthesis methods are also progressing rapidly, but the synthesis of 1,2,4-triazoles There are few methods that contain both trifluoromethyl and acyl groups in the molecular structure of azoles

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

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[0033] The present invention will be further described below in conjunction with specific embodiments.

[0034] Add aryl ethyl ketone (III), elemental iodine and dimethyl sulfoxide into a 35mL Schlenk tube according to the raw material ratio in Table 1, and add elemental iodine and phosphoric acid after the reaction is completed for 3-6 hours according to the reaction conditions in Table 2. Sodium hydrogen disodium, pyridine and trifluoroethylimide hydrazide (II), mixed and stirred evenly, continued to react according to the reaction conditions in Table 2 for 12-20 hours, filtered, sampled with silica gel, and purified by column chromatography to obtain the corresponding 3,4,5-trisubstituted 1,2,4-triazole compound (I), the reaction process is shown in the following formula:

[0035]

[0036] The raw material addition of table 1 embodiment 1~15

[0037]

[0038] Table 2

[0039]

[0040]

[0041] In Table 1 and Table 2, T is the reaction temperature, t is the rea...

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Abstract

The invention discloses a preparation method of a 3,4,5-trisubstituted 1,2,4-triazole compound. The preparation method comprises the following steps: adding aryl ethanone and iodine into dimethyl sulfoxide, conducting heating to 90-110 DEG C, performing reacting for 4-6 hours, adding iodine, sodium dihydrogen phosphate, pyridine and trifluoroethyl imine hydrazide into the organic solution, carrying out heating to 110-130 DEG C, performing reacting for 12-20 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3,4,5-trisubstituted 1,2,4-triazole compound. The preparation method is simple to operate, the initial raw materials are cheap and easy to obtain, the reaction does not need to be carried out under anhydrous and anaerobic conditions, heavy metal does not need to be used as a catalyst, the reaction can be easily expanded to gram level, operation is convenient, and the applicability of the method is widened.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of a 3,4,5-trisubstituted 1,2,4-triazole compound. Background technique [0002] 1,2,4-Triazole compound is an important nitrogen-containing five-membered heterocyclic ring, which widely exists in various 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. The introduction of trifluoromethyl groups into heterocyclic molecules can significantly improve the physicochemical properties of the parent compound, such as electronegativity, bioavailability, metabolic stability, and lipophilicity (Science 2007, 317, 1881). [0003] [0004] Nowadays, various methods for synthesizing 3,4,5-trisubstituted 1,2,4-triazoles have been reported...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07D405/06C07D409/06
CPCC07D249/08C07D405/06C07D409/06Y02A50/30
Inventor 陈铮凯张佳骏汤建华
Owner ZHEJIANG SCI-TECH UNIV
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