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Polymer-supported alpha-acylamino ketones: preparation and application in syntheses of 1,2,4-trisubstituted-1H-imidazoles.

ABSTRACT: 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.

SUBMITTER: Koci J

PROVIDER: S-EPMC2733363 | biostudies-literature | 2009 May-Jun

REPOSITORIES: biostudies-literature

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Polymer-supported alpha-acylamino ketones: preparation and application in syntheses of 1,2,4-trisubstituted-1H-imidazoles.

Kocí Jan J Pudelová Nadĕzda N Krchnák Viktor V

Journal of combinatorial chemistry 20090501 3

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-heterocyc ...[more]

PMID: 19354277

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