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Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]thiophenes and benzo[4,5]selenopheno[3,2-b]thiophenes using the Fiesselmann thiophene synthesis.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-04-02 , DOI: 10.1039/d0ob00300j Roman A Irgashev 1 , Nadezhda S Demina 1 , Gennady L Rusinov 1
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-04-02 , DOI: 10.1039/d0ob00300j Roman A Irgashev 1 , Nadezhda S Demina 1 , Gennady L Rusinov 1
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A series of 3-(hetero)aryl-substituted benzo[b]thieno[2,3-d]thiophenes, bearing various electron withdrawing groups at C-2 position of their scaffolds, were obtained using a convenient approach based on the Fiesselmann thiophene synthesis. To realize this strategy, the Friedel-Crafts acylation of (hetero)arenes with easily accessible 3-chlorobenzo[b]thiophene-2-carbonyl chlorides was initially performed to afford 3-chloro-2-(hetero)aroylbenzo[b]thiophenes. The latter ketones were treated either with methyl thioglycolate in the presence of DBU and calcium oxide powder or successively with sodium sulfide, an alkylating agent, containing methylene active component, and also DBU and calcium oxide, to form the desired benzo[b]thieno[2,3-d]thiophene derivatives. In addition, similar benzo[4,5]selenopheno[3,2-b]thiophene derivatives were prepared in the same manner using 3-bromobenzo[b]selenophen-2-yl substrates. The obtained functional derivatives of both benzo[b]thieno[2,3-d]thiophene and benzo[4,5]selenopheno[3,2-b]thiophene are of interest for further elaboration of organic semiconductor materials.
中文翻译：
使用菲塞尔曼噻吩合成法构建2,3-二取代的苯并[b]噻吩并[2,3-d]噻吩和苯并[4,5]硒代苯并[3,2-b]噻吩。
使用基于菲斯曼噻吩的便利方法，获得了一系列3-（杂）芳基取代的苯并[b]噻吩并[2,3-d]噻吩，它们在其支架的C-2位带有多个吸电子基团。合成。为了实现该策略，首先用容易获得的3-氯苯并[b]噻吩-2-羰基氯对（杂）芳烃进行弗里德尔-克拉夫茨酰化，得到3-氯-2-（杂）芳酰基苯并[b]噻吩。后者的酮在DBU和氧化钙粉末的存在下用巯基乙酸甲酯处理，或依次用硫化钠，含有亚甲基活性成分的烷基化剂以及DBU和氧化钙处理，形成所需的苯并[b] thieno [ 2,3-d]噻吩衍生物。此外，类似的苯并[4,5]硒代苯[3，使用3-溴苯并[b]硒吩-2-基底物以相同方式制备2-b]噻吩衍生物。所获得的苯并[b]噻吩并[2，3-d]噻吩和苯并[4，5]硒代苯并[3，2-b]噻吩的功能衍生物对于有机半导体材料的进一步加工是令人感兴趣的。
更新日期：2020-04-02
中文翻译：
使用菲塞尔曼噻吩合成法构建2,3-二取代的苯并[b]噻吩并[2,3-d]噻吩和苯并[4,5]硒代苯并[3,2-b]噻吩。
使用基于菲斯曼噻吩的便利方法，获得了一系列3-（杂）芳基取代的苯并[b]噻吩并[2,3-d]噻吩，它们在其支架的C-2位带有多个吸电子基团。合成。为了实现该策略，首先用容易获得的3-氯苯并[b]噻吩-2-羰基氯对（杂）芳烃进行弗里德尔-克拉夫茨酰化，得到3-氯-2-（杂）芳酰基苯并[b]噻吩。后者的酮在DBU和氧化钙粉末的存在下用巯基乙酸甲酯处理，或依次用硫化钠，含有亚甲基活性成分的烷基化剂以及DBU和氧化钙处理，形成所需的苯并[b] thieno [ 2,3-d]噻吩衍生物。此外，类似的苯并[4,5]硒代苯[3，使用3-溴苯并[b]硒吩-2-基底物以相同方式制备2-b]噻吩衍生物。所获得的苯并[b]噻吩并[2，3-d]噻吩和苯并[4，5]硒代苯并[3，2-b]噻吩的功能衍生物对于有机半导体材料的进一步加工是令人感兴趣的。
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