Reactions of 5-substituted (S)-1-acyl-3-[(E)-(dimethylamino)-methylidene]pyrrolidine-2-ones and (S)-3-[(E)-(dimethylamino)methylidene]tetrahydrofuran-2-ones with amines. Preparation of intermediates in the 'ring switching' synthesis of heteroarylalanine- and heteroaryllactic acid derivatives and their analogs

Authors
Skof, M Svete, J Stanovnik, B Golic-Grdadolnik, S
Citation
M. Skof et al., Reactions of 5-substituted (S)-1-acyl-3-[(E)-(dimethylamino)-methylidene]pyrrolidine-2-ones and (S)-3-[(E)-(dimethylamino)methylidene]tetrahydrofuran-2-ones with amines. Preparation of intermediates in the 'ring switching' synthesis of heteroarylalanine- and heteroaryllactic acid derivatives and their analogs, ACTA CHIM S, 46(4), 1999, pp. 567-586
Citations number
32
Categorie Soggetti
Chemistry
Journal title
ACTA CHIMICA SLOVENICA
ISSN journal
13180207 → ACNP
Volume
46
Issue
4
Year of publication
1999
Pages
567 - 586
Database
ISI
SICI code
1318-0207(1999)46:4<567:RO5(>2.0.ZU;2-Q
Abstract
5-Substituted (S)-1-acyl-3-[(E)-(dimethylamino)methylidene]pyrrolidin-2-one s 1-3 and (S)-3-[(E)-(dimethylamino)methylidene]-5-(methoxycarbonyl)tetrahy drofuran-2-one 4, chiral cyclic analogs of 2-substituted alkyl 3-(dimethyla mino)propenoates, were treated with alkyl, aryl, and heteroarylamines 6-25 under mild conditions to give 5-substituted (S)-3-[(substituted amino)methy lidene]pyrrolidin-2-ones 26-47 and (S)-3-[(E)-(substituted amino)methyliden e]-tetrahydrofuran-2-ones 48-52 as intermediates in a 'ring switching' synt hesis of 3-heteroarylalanine- and 3-heteroaryllactic acid derivatives and t heir analogs.