A New Route for the Synthesis of Trichloromethyl-1H-Benzo[d]imidazole and (1,2,3- Triazol)-1H-Benzo[d]imidazole Derivatives via Copper-Catalyzed N-Arylation and Huisgen Reactions

IF 1.7 3区 化学 Q3 CHEMISTRY, ORGANIC Current Organic Chemistry Pub Date : 2024-09-10 DOI:10.2174/0113852728322595240819045039
Manijeh Nematpour
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Abstract

: In this study, functionalized 2-(trichloromethyl)-1H-benzo[d]imidazole derivative with good yields was synthesized using a copper-catalyzed N-arylation reaction of 2-iodoaniline and trichloroacetonitrile. This reaction was performed by employing the catalytic value of copper (I) and 1,10-phenanthroline as the ligand in tetrahydrofuran solvent at 23°C. In the following, the reaction of the final product with phenylacetylene and sodium azide (Huisgen reaction) using the copper catalyst in water solvent at 23°C led to the synthesis of new (1,2,3-triazol)-1H-benzo[d]imidazole derivatives with the principles of green chemistry and suitable efficiency. The availability of raw materials and suitable catalysts, mild reaction conditions, and easy purification are among the advantages of this method for the synthesis of various multi-substituted benzo[d]imidazole and 1,2,3-triazole derivatives.
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通过铜催化的 N-芳基化和 Huisgen 反应合成三氯甲基-1H-苯并[d]咪唑和 (1,2,3- 三唑)-1H-苯并[d]咪唑衍生物的新途径
:本研究利用铜催化 2-碘苯胺和三氯乙腈的 N-芳基化反应,合成了具有良好产率的功能化 2-(三氯甲基)-1H-苯并[d]咪唑衍生物。该反应是在 23°C 的四氢呋喃溶剂中,利用铜 (I) 的催化值和 1,10-菲罗啉作为配体进行的。随后,利用铜催化剂在 23°C 水溶液中使最终产物与苯乙炔和叠氮化钠反应(Huisgen 反应),以绿色化学原理合成了新的(1,2,3-三唑)-1H-苯并[d]咪唑衍生物,并取得了适当的效率。该方法具有原料和催化剂易得、反应条件温和、易于纯化等优点,可用于合成各种多取代苯并[d]咪唑和 1,2,3- 三唑衍生物。
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来源期刊
Current Organic Chemistry
Current Organic Chemistry 化学-有机化学
CiteScore
3.70
自引率
7.70%
发文量
76
审稿时长
1 months
期刊介绍: Current Organic Chemistry aims to provide in-depth/mini reviews on the current progress in various fields related to organic chemistry including bioorganic chemistry, organo-metallic chemistry, asymmetric synthesis, heterocyclic chemistry, natural product chemistry, catalytic and green chemistry, suitable aspects of medicinal chemistry and polymer chemistry, as well as analytical methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by chosen experts who are internationally known for their eminent research contributions. The Journal also accepts high quality research papers focusing on hot topics, highlights and letters besides thematic issues in these fields. Current Organic Chemistry should prove to be of great interest to organic chemists in academia and industry, who wish to keep abreast with recent developments in key fields of organic chemistry.
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