title: New methodology for the N-alkylation of 2-amino-3-acylthiophenes.
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.
authors.affiliation: Medicinal Chemistry and Drug Action, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, Victoria, 3052, Australia.
authors.forename: Luigi
authors.initials: L
authors.lastname: Aurelio
authors.forename: Bernard L
authors.initials: BL
authors.lastname: Flynn
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Scammells
mesh_terms: D000478:Alkylation; D000586:Amination; D015394:Molecular Structure; D013876:Thiophenes / Q000138:chemical synthesis*
chemical_list: D013876:Thiophenes