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.
Kocí
Jan
J
Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Pudelová
Nadĕzda
N
Krchnák
Viktor
V
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