A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[b]thiophenes.
A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[b]thiophenes.
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DOI：
10.1039/d1ob00358e
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发表时间：
2021-05-12
影响因子：
3.2
通讯作者：
Kesharwani T
中科院分区：
文献类型：
--
作者：
Cunningham C;Cloyd M;Phillips A;Khan S;Whalen K;Kesharwani T
本研究开发了一种新的环境友好的碘介导的一锅碘化/烷基化反应方法，用于以2-炔基硫代苯甲醚为起始原料合成苯并[b]噻吩衍生物。采用温和的反应条件，以1，3-二酮基底物为亲核剂，以不同取代的炔丙醇为环化前体和烷基化试剂，高产率地合成了多种2，3-二取代苯并[b]噻吩类化合物。这种方法一步就形成了一系列复杂的结构。此外，还设计了一种策略，用于丙叉醇的一锅碘环化/氧化生成羰基功能化的苯并[b]噻吩类结构。这些绿色的一锅反应过程旨在减少废物和副产物，同时在苯并[b]噻吩结构上产生复杂的取代模式。报道的方法可以用来合成更多官能化的苯并[b]噻吩结构，这些结构可以用于生物医学和有机电子应用。为了合成高功能化的3-碘苯并[b]噻吩衍生物，开发了一步法合成3-碘代苯并[b]噻吩衍生物。
In this study, a new environmentally benign iodine-mediated one-pot iodocyclization/alkylation strategy for the synthesis of benzo[b]thiophene derivatives starting from 2-alkynylthioanisoles was developed. The synthesis of a diverse population of 2,3-disubstituted benzo[b]thiophenes was achieved in high yields by employing moderate reaction conditions using 1,3-dicarbonyl substrates as the nucleophile and various substituted propargyl alcohols as both the cyclization precursor and the alkylating agent. This method resulted in the formation of a series of complex structures obtained in a single step. Additionally, a strategy was devised for the one pot iodocyclization/oxidation of propargyl alcohols into carbonyl functionalized benzo[b]thiophene structures. These green one-pot reaction processes were designed to reduce wastes and byproducts while generating a complex substitution pattern on the benzo[b]thiophene structure. The reported methodologies may be used to synthesize more functionalized benzo[b]thiophene structures that can be used in both biomedical and organic electronic applications. A successive one-pot iodocyclization alkylation strategy was developed to synthesize highly functionalized 3-iodobenzo[b]thiophenes derivatives.
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影响因子：
5.2
作者：
Krzyzanowski, Adrian;Saleeb, Michael;Elofsson, Mikael
通讯作者：
Elofsson, Mikael
影响因子：
1.8
作者：
Kesharwani, Tanay;Kornman, Cory T.;Royappa, Andrew D.
通讯作者：
Royappa, Andrew D.
影响因子：
5.2
作者：
Kasare, Sanghratna;Bankar, Siddheshwar K.;Ramasastry, S. S. V.
通讯作者：
Ramasastry, S. S. V.
影响因子：
2.1
作者：
Han, Jie;Wang, Qiong;Meng, Jiben
通讯作者：
Meng, Jiben
影响因子：
5.2
作者：
Guilarte, Veronica;Fernandez-Rodriguez, Manuel A.;Sanz, Roberto
通讯作者：
Sanz, Roberto