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Issue 13, 2011
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New methodology for the N-alkylation of 2-amino-3-acylthiophenes

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Abstract

2-Amino-3-acylthiophenes are known to allosterically modulate the A1adenosine receptor and are also used as intermediates in the synthesis of therapeutic agents and pharmacophores such as thienoazepines and thienopyrimidines. The N-alkylation of 2-aminothiophenes has been notoriously difficult to accomplish under mild conditions and there are very few examples of N-alkylated 2-aminothiophenes in the literature, all of which use forcing conditions to effect the alkylation. Here we describe the synthesis of such compounds under mild conditions utilising 2-carbamoylamino and 2-acylamino-3-acylthiophenes with caesium carbonate, and tetrabutylammonium iodide in DMF.

Graphical abstract: New methodology for the N-alkylation of 2-amino-3-acylthiophenes

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Publication details

The article was received on 13 Dec 2010, accepted on 29 Mar 2011 and first published on 29 Mar 2011


Article type: Paper
DOI: 10.1039/C0OB01156H
Org. Biomol. Chem., 2011,9, 4886-4902

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    New methodology for the N-alkylation of 2-amino-3-acylthiophenes

    L. Aurelio, B. L. Flynn and P. J. Scammells, Org. Biomol. Chem., 2011, 9, 4886
    DOI: 10.1039/C0OB01156H

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