One-pot two-component [3 + 2] cycloaddition/annulation protocol for the synthesis of highly functionalized thiophene derivatives.
One-pot two-component [3 + 2] cycloaddition/annulation protocol for the synthesis of highly functionalized thiophene derivatives.
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DOI：
10.1021/jo200685e
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发表时间：
2011-08
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影响因子：
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通讯作者：
G. Nandi;S. Samai;M. Singh
中科院分区：
文献类型：
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作者：
G. Nandi;S. Samai;M. Singh
通过 4-二甲基氨基吡啶 (DMAP) 促进的 1-2 (C-S) 和 3-4 (C-C) 键连接，开发了一种高效且实验快速的合成迄今未报道的 2,3-二碳烷氧基-4-芳酰基/杂芳酰基/烷酰基噻吩的方案。最佳情况下，当 β-氧代二硫酯和乙炔二甲酸二烷基酯在 DCM 中、在 DMAP 存在下于室温搅拌时，反应仅需 3-5 分钟。该方法可以清洁且通用地合成以前无法获得且合成要求较高的含有二茂铁基的噻吩。该过程的速度、实验简便性和高产率是对访问这一重要子结构的现有方法的改进。
An efficient and experimentally rapid protocol for the synthesis of hitherto unreported 2,3-dicarboalkoxy-4-aroyl/heteroaroyl/alkanoyl thiophenes has been developed via 1-2 (C-S) and 3-4 (C-C) bond connections promoted by 4-dimethylaminopyridine (DMAP). Optimally, the reaction takes only 3-5 min when β-oxodithioester and dialkyl acetylenedicarboxylate are stirred in DCM at room temperature in the presence of DMAP. This method allows a clean and general synthesis of previously inaccessible and synthetically demanding thiophenes containing the ferrocenyl group. The speed, experimental ease, and high yields of this process are improvements over existing methods to access this important substructure.