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.
Originalsprog | Engelsk |
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Tidsskrift | Journal of Combinatorial Chemistry |
Vol/bind | 10 |
Udgave nummer | 3 |
Sider (fra-til) | 447-455 |
Antal sider | 9 |
ISSN | 1520-4766 |
DOI | |
Status | Udgivet - maj 2008 |
Eksternt udgivet | Ja |
ID: 321827663