Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones

Authors
Ghelfi, F Ghirardini, G Libertini, E Forti, L Pagnoni, UM
Citation
F. Ghelfi et al., Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones, TETRAHEDR L, 40(49), 1999, pp. 8595-8597
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
49
Year of publication
1999
Pages
8595 - 8597
Database
ISI
SICI code
0040-4039(199912)40:49<8595:EAT3F3>2.0.ZU;2-7
Abstract
3-Benzylimino-2-pyrrolidinones can be prepared in good yield by heating 3-c hloro-4-chloromethyl-2-pyrrolidinones, benzylamine and NaI in THF at 80 deg rees C. An endo-dehydrohalogenation followed by a SN2' substitution on the intermediate allyl chloride, and finally a shift of the exo-double bond to Delta(3) with attendant tautomerization, appears to be the most probable re action mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.