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

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Standard

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

Harvard

Le Quement, ST, Nielsen, TE & Meldal, M 2008, 'Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes', Journal of Combinatorial Chemistry, bind 10, nr. 3, s. 447-455. https://doi.org/10.1021/cc700199n

APA

Le Quement, S. T., Nielsen, T. E., & Meldal, M. (2008). Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes. Journal of Combinatorial Chemistry, 10(3), 447-455. https://doi.org/10.1021/cc700199n

Vancouver

Le Quement ST, Nielsen TE, Meldal M. Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes. Journal of Combinatorial Chemistry. 2008 maj;10(3):447-455. https://doi.org/10.1021/cc700199n

Author

Le Quement, Sebastian T. ; Nielsen, Thomas E. ; Meldal, Morten. / Solid-phase synthesis of aryl-substituted thienoindolizines : Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes. I: Journal of Combinatorial Chemistry. 2008 ; Bind 10, Nr. 3. s. 447-455.

Bibtex

@article{0474bfec9abc4373b53e80669d1318ba,
title = "Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes",
abstract = "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.",
author = "{Le Quement}, {Sebastian T.} and Nielsen, {Thomas E.} and Morten Meldal",
year = "2008",
month = may,
doi = "10.1021/cc700199n",
language = "English",
volume = "10",
pages = "447--455",
journal = "ACS Combinatorial Science",
issn = "2156-8952",
publisher = "ACS Publications",
number = "3",

}

RIS

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