Preparation of 1,5-Disubstituted Pyrrolidin-2-ones

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...

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Veröffentlicht in:Journal of organic chemistry 2000-07, Vol.65 (14), p.4364-4369
Hauptverfasser: Katritzky, Alan R, Mehta, Shamal, He, Hai-Ying, Cui, Xilin
Format: Artikel
Sprache:eng
Schlagworte:
Drug Design
Indicators and Reagents
Pyrrolidinones - chemical synthesis
Pyrrolidinones - chemistry
Structure-Activity Relationship
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000219w