Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes
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Solid-phase synthesis of aryl-substituted thienoindolizines : Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes. / Le Quement, Sebastian T.; Nielsen, Thomas E.; Meldal, Morten.
I: Journal of Combinatorial Chemistry, Bind 10, Nr. 3, 05.2008, s. 447-455.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Solid-phase synthesis of aryl-substituted thienoindolizines
T2 - Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes
AU - Le Quement, Sebastian T.
AU - Nielsen, Thomas E.
AU - Meldal, Morten
PY - 2008/5
Y1 - 2008/5
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=45149116915&partnerID=8YFLogxK
U2 - 10.1021/cc700199n
DO - 10.1021/cc700199n
M3 - Journal article
C2 - 18386932
AN - SCOPUS:45149116915
VL - 10
SP - 447
EP - 455
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
SN - 2156-8952
IS - 3
ER -
ID: 321827663