Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes

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The solid-phase synthesis of a range of novel heterocyclic scaffolds based on the thiophene ring system, including thienoindolizines and aryl-substituted thiophenes, is presented. Specifically, a sequential methodology for the decoration of thienoindolizine scaffolds has been developed. This method involves a highly efficient and diastereoselective intramolecular Pictet-Spengler reaction, a quantitative and regioselective bromination of the thiophene ring, and a final Suzuki cross-coupling with an arylboronic acid. Crude products were generally obtained in high purities (>90%). In addition, an investigation on the acidic and electronic effects governing the rate of the Pictet-Spengler reactions was performed. Finally, a range of substituted thiophenes was attached to solid supports and subjected to the regioselective bromination and Suzuki cross-coupling reactions, thus providing substituted thiophenes with high purities of crude products.

TidsskriftJournal of Combinatorial Chemistry
Udgave nummer3
Sider (fra-til)447-455
Antal sider9
StatusUdgivet - maj 2008
Eksternt udgivetJa

ID: 321827663