5-alkenyl-1, 4-disubstituted-1, 2, 3-triazole compound, preparation method and application thereof

Abstract

The invention discloses a 5-alkenyl-1, 4-disubstituted-1, 2, 3-triazole compound, a preparation method and application thereof. The 5-alkenyl-1, 4-disubstituted-1, 2, 3-triazole compound has the structural formula as follows, R1 is -COOMe, phenyl, p-fluorophenyl or p-methylphenyl; R2 is phenyl, n-hexyl or p-methylphenyl; and R 3 is phenyl, phenmethyl, n-butyl or n-octyl. The preparation method has good reaction selectivity, simple and feasible steps, low price of the raw materials used in the reaction and easily obtained raw materials, and is beneficial to industrialized production; furthermore, the compound can be used for preparing pesticide or bactericide of fruit trees, melons, beans, solanaceous fruits, flowers and the like, has good desinsection and sterilizing effects and is beneficial to environmental protection.

Description

technical field [0001] The invention relates to the field of preparation of triazole compounds, in particular to a 5-alkenylated-1,4 substituent-1,2,3-triazole compound and its preparation method and application. Background technique [0002] 1,2,3-triazole compound is an important five-membered nitrogen heterocyclic compound, which has good stability to acid and alkali, oxidant and reducing agent, and is widely used in pesticides and medicines, such as: other Zobactam (tazobactam) and its derivatives are powerful β-lactamase inhibitors; in the field of antibacterial agents, the triazole-containing structure also helps to improve the metabolism of drugs; modifying pyrimidine nucleosides with triazole structures, Drugs can be made both antiviral and cytotoxic. In addition, people use triazole chemicals as scaffolds to modify the electrode surface, and the same concept is also used for the synthesis of dual-active drugs. In addition, triazole compounds are also important org...

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Problems solved by technology

[0003] Due to the good stability of 1,2,3-triazole compounds, it is difficult to directly modify them, and the current literature reports are relatively few

In recent years, Professor Lutz Ackermann has successfully achieved the arylation of 1,2,3-triazole compounds using various aromatic halide compounds under the catalysis of palladium or copper, such as: [1]Chuprakov, S.; Chernyak, N. ; Dudnik, A.S.; Gevorgyan, V., Direct Pd-Catalyzed Arylation of 1,2,3-Triazoles, Org. Lett.2007, 9, 2333; [2] Ackermann, L.; Potukuchi, H.K.; Landsberg, D. ; Vicente, R., Copper-Catalyzed “Click” Reaction / Direct Arylation Sequence: Modular Syntheses of 1, 2, 3-Triazoles, Org. Lett. 2008, 10, 3081; [3] Ackermann, L.; Vicente, R. , Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium (0) Catalyst for C-H Bond Cleavages in the Presence of Air, Org. Lett. In pressed and [4] Ackermann, L.; Vicente, R.; Born, R. ., Palladium-Catalyzed Direct Arylations of 1,2,3-Triazoles with ArylChlorides using Conventional Heating, Adv.Synth.Catal.2008,350,741; these methods all inevitably produce the by-product of hydrogen halide, which is harmful to the environment Causes certain pollution, and the atomic economy of the reaction is not high, and the steps are more complicated

Larger restrictions caused by modification of the 1,2,3-triazole ring

Professor Wu Yongming synthesized 5-alkenylation-1,4-disubstituted-1,2,3-triazole compound by synthesizing 5-iodo-1,4-disubstituted-1,2,3-triazole compound, and then reacted with terminal olefin to synthesize 5-alkenylated-1,4-disubstituted-1, 2,3-triazole compounds, [6] J.Deng, Y.M.Wu, Q.Y.Chen., The First Example for the Cross Coupling Reaction ofIodo-1,2,3-triazoles Catalyzed by Palladium, Synth.2005, 16, 2730 ; This method has complicated synthesis steps and expensive raw materials, which greatly restrict its application

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