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標題: 利用一鍋三步連續反應以形成2,3-雙取代基苯並[b]?吩及多官能基芳香化合物之合成研究
Study in the One-Pot Three-Step Synthesis of 2,3-Disubstituted Benzo[B]Thiophenes and Multi- Functionalized Arenes
作者: 陳耀鐘
關鍵字: 化學類

摘要: 發展對環境更乾淨、安全、且有效的有機化學合成方法是目前很重要的研究領域之一,而如何降低使用能源及減少化學廢棄物皆是其重要目標。為達上述目的,利用一鍋多步連續反應之合成方法,即因其反應過程不必純化分離反應中間物,故它是很好且簡單的選擇方法。苯並[b]噻吩是製備許多藥物及材料之重要中間物,其多種衍生物被發現具有抗腫瘤、抗細菌、抗過敏症、及抗發炎等效果。例如raloxifene 已經被發現是具有很好療效的選擇性雌激素受體調節器。另一方面,多官能基芳香化合物則是常用且重要的有機合成中間物。因此如何有效合成這些重要化合物是急迫且具挑戰性的。目前已知有許多製備苯並[b]噻吩衍生物及多官能基芳香化合物之文獻報導,其使用方法主要是利用傳統一步反應完成,且純化分離反應中間物再接另一步反應。截至目前為止,比較少有文獻報導直接利用一鍋多步連續反應之方法合成具療效之藥物(如raloxifene)及重要的多官能基芳香化合物。因此,本研究計畫主要是利用一鍋三步連續反應以形成2,3-雙取代基苯並[b]噻吩及多官能基芳香化合物之合成,並將直接利用其合成raloxifene。
Recently, it has been gained more attention to search for alternative cleaner, safer, andenvironmentally friendly technologies in organic synthetic chemistry. For this purpose, thereduction of wastes along with the use of environmentally friendly reagents and catalysts areimportant parameters to achieve more sustainable processes. In addition to those, one-potprocedures are able to allow the decrease of energy consuming steps such as separation andpurification of intermediates. These transformations known as tandem, domino, or cascadereactions have become an important area of research in organic chemistry since they improve atomeconomy, energy, and raw materials consumption. The simplest way to perform a multistepsynthesis is to perform the consecutive steps not only in the same vessel but also under the samereaction conditions. However, when this is not possible, the one-pot reaction is carried out in two ormore stages under different optimized reaction conditions in order to reach the maximum selectivityto the target product. With these objectives and the conjunction of our recent studies in couplingreactions, this project will focus on the one-pot three-step synthesis of 2,3-disubstitutedbenzo[b]thiophenes and multi-functionalized arenes.Benzo[b]thiophene has been attracted much attention as a useful building block in the preparationof the numerous important products in the fields of pharmaceutical, biological, and material science.Some of benzo[b]thiophene derivatives have been found to exhibit as potent antitumor, antibacterial,antibiotic, antimitotic, antipsychotic, antifungal, antiinflammatory, antiallergic, and antimicrobialagents. For example, raloxifene has been found to be the unique selective estrogen receptormodulators (SERMs). On the other hand, multi-functionalized arenes are important and widely usedas a building block in organic synthesis for a long time. For example, 2-bromo-4,5-dimethoxybenzonitrilehas been used to synthesize the [1]benzothieno[3,2-d]pyrimidines derivatives as theinhibitor of the epidermal growth factor receptor tyrosine. Thus, the research directed towardconcise, new syntheses of 2,3-disubstituted benzo[b]thiophenes and multi-functionalized arenes hasbeen actively pursued in recent years. However, it is still less well established to use one-potmultiple-step process for the preparation of those important molecules. Therefore, our studies inthis project will mainly involve:1. Study in copper-mediated a simple and efficient one-pot synthesis of 2-aryl-3-sulfenylbenzo[b]thiophenes from commercially available o-iodothioanisole via Sonogashira-typereaction, iodocyclization, and Ullmann-type reaction.2. Study in copper-mediated a simple and efficient one-pot synthesis of 2-aryl-3-cyanobenzo[b]thiophenes from commercially available o-iodothioanisole via Sonogashira-typereaction, iodocyclization, and cyanation reaction: An alternative and efficient route toraloxifene.3. Study in copper-mediated a simple and efficient one-pot synthesis of 2-aryl-3-(arylethynyl)benzo[b]thiophenes from commercially available o-iodothioanisole via Sonogashira-typereaction, iodocyclization, and Sonogashira-type reaction.4. Study in the selective functionalization of aryl C-H bonds: A simple and efficient one-potthree-step synthesis of multi-functionalized arenes from simple arenes via iodination,bromination, and Ullmann-type reaction.
其他識別: NSC100-2113-M005-006
Appears in Collections:化學系所



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