Polymer-supported alpha-acylamino ketones: preparation and application in syntheses of 1,2,4-trisubstituted-1H-imidazoles.
Polymer-supported alpha-acylamino ketones were prepared from resin-bound amines, bromoketones, and carboxylic acids. Selective monoalkylation of amines by bromoketones was carried out via 4-nitrobenzenesulfonamides. There was a striking difference in the reaction outcome between 2-Nos and 4-Nos derivatives. Alpha-acylamino ketones were converted to imidazoles. The cyclization was performed on resin, allowing further polymer-supported elaboration of imidazoles including synthesis of bis-heterocyclic compounds. A small combinatorial array of imidazoles was synthesized. Target compounds were prepared under mild conditions using commercially available building blocks for the introduction of three points of diversity.
Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Jan
J
Kocí
Nadĕzda
N
Pudelová
Viktor
V
Krchnák
D000215:Acylation; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000191:economics / Q000379:methods*; D003500:Cyclization; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry / Q000191:economics
D000588:Amines; D002264:Carboxylic Acids; D007093:Imidazoles; D007659:Ketones; D054852:Small Molecule Libraries