Preparation of 1,5-disubstituted pyrrolidin-2-ones.
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.
Katritzky
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Center for Heterocyclic Chemistry, Department of Chemistry, University of Florida, Gainesville 32611-7200, USA.
Mehta
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S
He
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Cui
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D015195:Drug Design; D007202:Indicators and Reagents; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
D007202:Indicators and Reagents; D011760:Pyrrolidinones