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Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles Through a One-Pot Three Component Reaction of Boronic Acids, Sodium Azide and Active Methylene Compounds Under Ball-Milling Conditions
Polycyclic Aromatic Compounds ( IF 2.4 ) Pub Date : 2020-04-30 , DOI: 10.1080/10406638.2020.1757473
Rahman Hosseinzadeh 1 , Fatemeh Fathalipour 1 , Mahmood Tajbakhsh 1 , Mohammad Mavvaji 1 , Mona Pooryousef 1
Affiliation  

Abstract

In this study, we report a mild and efficient one-pot synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via a three-component reaction of aryl boronic acids with sodium azide and active methylene compounds under ball-milling condition. In order to determine optimized reaction conditions, several grinding auxiliaries (basic, neutral and acidic alumina, silica gel, K10 and KSF), bases (DBU, DABCO, piperidine, triethylamine, potassium t-butoxide and potassium carbonate) and copper salts under ball-milling conditions were examined. Using the optimized condition procedure, a wide variety of 1,4,5-trisubstituted 1,2,3-triazole derivatives were prepared in very good yields. All products were well-characterized by 1H-NMR and 13C-NMR spectroscopy. This environmentally friendly protocol offers several advantages including high yields of products, relatively short reaction time and simple work-up procedure.



中文翻译:

球磨条件下硼酸、叠氮化钠和活性亚甲基化合物的一锅三组分反应合成1,4,5-三取代1,2,3-三唑

摘要

在这项研究中,我们报道了通过芳基硼酸与叠氮化钠和活性亚甲基化合物在球磨条件下的三组分反应,温和高效地一锅法合成 1,4,5-三取代的 1,2,3-三唑。健康)状况。为了确定优化的反应条件,几种研磨助剂(碱性、中性和酸性氧化铝、硅胶、K10 和 KSF)、碱(DBU、DABCO、哌啶、三乙胺、丁醇钾和碳酸钾)和铜盐在球下-检查研磨条件。使用优化的条件程序,以非常好的收率制备了多种 1,4,5-三取代 1,2,3-三唑衍生物。所有产品均通过1 H-NMR 和13C 核磁共振波谱。这种环保协议提供了几个优点,包括产品产量高、反应时间相对较短和后处理程序简单。

更新日期:2020-04-30
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