Solid-phase synthesis of 1,2,5-trisubstituted 4-imidazolidinones |
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Authors: | Rinnová Markéta Vidal Agnès Nefzi Adel Houghten Richard A |
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Institution: | Torrey Pines Institute for Molecular Studies, 3550 General Atomics Court, San Diego, California 92121, USA. |
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Abstract: | An efficient method for the preparation of 1,2,5-trisubstituted 4-imidazolidinones is presented. The synthetic approach is based on the formation of an N-1-(benzotriazol-1-yl)alkyl] moiety on the amino group of a MBHA resin-bound amino acid. The nucleophilic substitution of the benzotriazole group with an amidic nitrogen results in the formation of a five-membered imidazolidinone ring. The reaction is nonstereospecific and produces diastereomers in ratios that vary depending on the substituents on the ring. A variety of N-alpha-alkylated amino acids were cyclized with aromatic, aliphatic, and heterocyclic aldehydes to determine optimal reaction conditions and to select building blocks for the future preparation of a large, diverse range of individual trisubstituted imidazolidinones as well as a mixture-based combinatorial library. |
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