title: Preparation of 1,5-disubstituted pyrrolidin-2-ones.
abstract: 1,5-Disubstituted pyrrolidin-2-ones 18a-g, 19a-h, and 20a-f were synthesized in good to excellent yields via the nucleophilic substitution of 5-(benzotriazol-1-yl)-1-substituted-pyrrolidin-2-ones 9 with allylsilanes, organozinc reagents, and phosphorus compounds. Compounds 9 and 5-(benzotriazol-2-yl)-1-substituted-pyrrolidin-2-one isomers 10 are readily prepared in total 70-84% yields from 2, 5-dimethoxy-2,5-dihydrofuran (7), primary amines 8, and benzotriazole; 9 and 10 react identically with nucleophiles.
authors.affiliation: Center for Heterocyclic Chemistry, Department of Chemistry, University of Florida, Gainesville 32611-7200, USA.
authors.forename: A R
authors.initials: AR
authors.lastname: Katritzky
authors.forename: S
authors.initials: S
authors.lastname: Mehta
authors.forename: H Y
authors.initials: HY
authors.lastname: He
authors.forename: X
authors.initials: X
authors.lastname: Cui
mesh_terms: D015195:Drug Design; D007202:Indicators and Reagents; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D007202:Indicators and Reagents; D011760:Pyrrolidinones