Department of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, Fl 32514, USA.
Org Biomol Chem. 2021 May 12;19(18):4107-4117. doi: 10.1039/d1ob00358e.
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.
在这项研究中，开发了一种新的环境友好型碘介导的一锅法碘环化/烷基化策略，用于从 2-炔基硫代苯甲醚合成苯并[b]噻吩衍生物。通过使用中等反应条件，以 1,3-二羰基底物作为亲核试剂，各种取代的丙炔醇作为环化前体和烷基化试剂，实现了多种 2,3-二取代苯并[b]噻吩的高产率合成。该方法可在一步反应中得到一系列复杂结构。此外，还设计了一种将丙炔醇一锅法碘环化/氧化为羰基官能化苯并[b]噻吩结构的策略。这些绿色的一锅反应过程旨在减少废物和副产物的生成，同时在苯并[b]噻吩结构上产生复杂的取代模式。所报道的方法学可用于合成更多功能化的苯并[b]噻吩结构，这些结构可用于生物医学和有机电子应用。
