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 A(1) adenosine 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.
Original languageEnglish
Pages (from-to)4886 - 4902
Number of pages17
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number13
Publication statusPublished - 2011

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