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A kind of preparation method of 1,4-disubstituted-1,2,3-triazole compound
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A technology of triazole and disubstitution, which is applied in the field of synthesis of multi-substituted triazole compounds, can solve the problem of high yield and achieve the effects of simple catalytic system, mild reaction conditions and convenient operation
Inactive Publication Date: 2017-02-22
HENAN NORMAL UNIV
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However, both of these methods use the organic base DBU as a catalyst, and the yield is high, and the reagent DMSO, which is harmful to the environment, is used (Angewandte Communications, 2014, 53: 10420-10424.)
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Embodiment 1
[0016] Weigh phenylacetaldehyde (120mg, 1mmol) and phenyl azide (119mg, 1mmol), measure ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF 4 ) 3mL, add NaOH (0.4mg, 0.01mmol), stir at room temperature, magnetically stir, TLC monitors the reaction, after 10min, the reaction is over, there is solid precipitation, ether extraction, drying, you can get 1,4-diphenyl-1H- 1,2,3-Triazole, the yield is 95%.
Embodiment 2
[0018] Weigh phenylacetaldehyde (120mg, 1mmol) and phenyl azide (119mg, 1mmol), measure ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF 4 ) 3mL, add NaOH (8mg, 0.2mmol), room temperature, magnetic stirring, TLC monitoring reaction, after 10min, the reaction is over, there is solid precipitation, ether extraction, drying, you can get 1,4-diphenyl-1H-1 , 2,3-triazole, yield 96%.
Embodiment 3
[0020] Weigh phenylacetaldehyde (120mg, 1mmol) and phenyl azide (119mg, 1mmol), measure ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF 4 ) 3mL, add KOH (0.56mg, 0.01mmol), stir at room temperature, magnetically stir, TLC monitors the reaction, after 10min, the reaction is over, there is solid precipitation, ether extraction, drying, you can get 1,4-diphenyl-1H- 1,2,3-triazole, yield 93%.
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Abstract
The invention discloses a 1,4-disubstituted-1,2,3-triazole compound preparation method which comprises the following steps: (1) adding a catalyst inorganic base in an ionic liquid, wherein the catalyst inorganic base is potassium hydroxide or sodium hydroxide, and the ionic liquid is 1-butyl-3-methylimidazolium tetrafluoroborate, 1-Buthyl-3-methylidazolium bromide or 1-butyl-3-methylimidazolium hexafluorophosphate; (2) adding raw material phenylacetaldehyde or substituted phenylacetaldehyde and pinacolborane in the mixed system formed in the step (1), reacting under the room temperature at the stirring condition, separating out the solid phase after reaction finishing, extracting diethyl ether, and drying to obtain the 1,4-disubstituted-1,2,3-triazole compound. The preparation method has the advantages that the catalytic system is simple, the operation is convenient, the reaction condition is mild, and reactive solvents can be recycled repeatedly.
Description
technical field [0001] The invention belongs to the technical field of synthesis of multi-substituted triazole compounds, and in particular relates to a preparation method of 1,4-disubstituted-1,2,3-triazole compounds. Background technique [0002] Nitrogen-containing heterocyclic compounds have a wide range of biological activities and application values, and their synthesis, structure optimization and development have always been research hotspots in biochemistry, organic chemistry, materials chemistry, analytical chemistry, and polymer chemistry. 1,2,3-Triazole and its derivatives have good pharmacological activities, such as anticancer, antibacterial, antiviral, anticonvulsant, etc., and have been widely used in drug development and structural modification. Recent studies have also found that some 1,2,3-triazole compounds can also be used as HIV protease inhibitors, histone deacetylase inhibitors, and biological probes. In addition, 1,2,3-triazole compounds can also be ...
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