title: Solid-phase synthesis of piperazinones via disrupted Ugi condensation.
abstract: The first application of aziridine aldehyde dimers in solid-phase synthesis is reported. The solid-supported disrupted Ugi condensation between an aziridine aldehyde dimer, isonitrile, and backbone-anchored amino acids delivered N-acyl aziridine intermediates, which were reacted with nucleophiles to yield the corresponding piperazinones. Subsequent cleavage from the resin provided a diverse set of 2,3,6-trisubstituted piperazinones starting from various amino acids, aziridine aldehydes, and nucleophiles.
authors.affiliation: Département de Pharmacologie, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke , Sherbrooke, QC, Canada J1H 5N4.
authors.forename: Adam P
authors.initials: AP
authors.lastname: Treder
authors.forename: Marie-Claude
authors.initials: MC
authors.lastname: Tremblay
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin
authors.forename: Eric
authors.initials: E
authors.lastname: Marsault
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D001388:Aziridines; D010879:Piperazines