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A kind of synthetic method of 1,2,3-triazole compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve problems such as product structure limitations, achieve high reaction specificity, improve reaction yield and product quality, and have no harsh reaction conditions.

Active Publication Date: 2019-01-29
天驰药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] Although there are many methods for constructing triazole rings, there are still some limitations. For example, explosive azide compounds and diazonium salts need to be used as raw materials for cycloaddition reactions in most reactions, and some product structures are limited to those containing aromatic compounds. substituted compounds, etc.

Method used

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  • A kind of synthetic method of 1,2,3-triazole compound
  • A kind of synthetic method of 1,2,3-triazole compound

Examples

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Embodiment 1

[0034] A synthesis method of a 1,2,3-triazole compound proposed by the present invention, the 1,2,3-triazole compound is 4,5-dimethyl-1H-1,2,3-triazole Azole, the synthetic method of described 4,5-dimethyl-1H-1,2,3-triazole comprises the following steps:

[0035] Synthesis of S1, 3-p-toluenesulfonylhydrazono-2-butanol

[0036] Dissolve 9.03g of 2,3-butanediol in 40ml of dichloroethane, slowly add 11.5g of sodium bromate and 7.81g of sodium bisulfite to the solution, raise the temperature to 40°C, and stir within 1 hour Add 19.57g p-toluenesulfonyl hydrazide in batches, and HPLC tracks and detects the reaction process until the peak area of ​​2,3-butanediol in HPLC is less than 0.2%, and adding a mass fraction of 10% sodium hydroxide aqueous solution to the reaction solution The pH value is 7, the reaction solution is concentrated to half volume and then cooled to room temperature, the precipitated inorganic salt is filtered, and the filtrate is distilled under reduced pressur...

Embodiment 2

[0042] A synthesis method of a 1,2,3-triazole compound proposed by the present invention, the 1,2,3-triazole compound is 4,5-dimethyl-1H-1,2,3-triazole Azole, the synthetic method of described 4,5-dimethyl-1H-1,2,3-triazole comprises the following steps:

[0043] Synthesis of S1, 3-benzenesulfonylhydrazono-2-butanol

[0044] Dissolve 9.02g of 2,3-butanediol in 40ml of acetonitrile, slowly add 12.6g of sodium bromate and 8.24g of sodium bisulfite to the solution, raise the temperature to 50°C, and add in batches within 1 hour under stirring 18.62g of benzenesulfonyl hydrazide, HPLC tracking and detection of the reaction process until the peak area of ​​2,3-butanediol in the HPLC is less than 0.2%, adding a mass fraction of 10% sodium hydroxide aqueous solution to the reaction solution until the pH value of the solution is 7 , the reaction solution was concentrated to half the volume and then cooled to room temperature, the precipitated inorganic salt was filtered, and the filt...

Embodiment 3

[0050] A synthesis method of a 1,2,3-triazole compound proposed by the present invention, the 1,2,3-triazole compound is 4,5-diphenyl-1H-1,2,3-triazole Azole, the synthetic method of described 4,5-diphenyl-1H-1,2,3-triazole comprises the following steps:

[0051] S1, Synthesis of 1,2-diphenyl-1-methanesulfonylhydrazono-2-ethanol

[0052] Dissolve 21.26g of 1,2-diphenyl-1,2-ethanediol in 40ml of carbon tetrachloride, slowly add 14.8g of sodium bromate and 9.62g of sodium bisulfite into the solution, and raise the temperature to 60°C. Under stirring condition, in 1 hour, add 12.5g methanesulfonyl hydrazide in batches, simultaneously HPLC tracks and detects reaction progress to the peak area of ​​1,2-diphenyl-1,2-ethanediol in HPLC is less than 0.2%, to The reaction solution is added with a mass fraction of 10% sodium hydroxide aqueous solution until the pH value of the solution is 7, the reaction solution is concentrated to half the volume and then cooled to room temperature, t...

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Abstract

The invention belongs to the technical field of preparation of pharmaceutical and chemical intermediates and particularly relates to a method for synthesizing a 1, 2, 3-triazole compound. The 1, 2, 3-triazole compound has substituents at 4th and 5th sites. The method comprises that a vicinal diol compound and a hydrazine derivative undergo a condensation reaction under oxidation of an oxidizing agent to produce an intermediate, and the intermediate and ammonia gas undergo a cyclization reaction after condensation under oxidation of an oxidizing agent to produce the 1, 2, 3-triazole compound with substituents at 4th and 5th sites. The method has high reaction specificity, safety and treatment convenience, belongs to the environment-friendly reaction type, needs mild post-treatment conditions, realizes oxidizing agent recovery and reuse, has simple processes and a high reaction yield, produces high quality products and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of preparation of pharmaceutical and chemical intermediates, in particular to a method for synthesizing 1,2,3-triazole compounds. Background technique [0002] 1,2,3-Triazole compounds are five-membered aromatic heterocyclic rings containing multiple nitrogen atoms, and have a variety of unique physical and chemical properties. They are important structural units of a class of drug molecules, especially click chemistry was proposed and After the discovery, a batch of drugs containing the structure of 1,2,3-triazole compounds were discovered and screened out. In recent years, scholars at home and abroad have paid more and more attention to the research of such compounds, and finding efficient and selective synthetic methods for the construction of 1,2,3-triazole compounds has become an issue of increasing concern to organic chemists and medicinal chemists. There are many literature reports on the preparation...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/04C07D249/06
CPCC07D249/04C07D249/06
Inventor 苏庆丰张海清那日松楚静波袁国龙苏熙盛张力天张瑞琪
Owner 天驰药业有限公司
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