3-Benzylimino-2-pyrrolidinones can be prepared in good yield by heating 3-chloro-4-chloromethyl-2-pyrrolidinones, benzylamine and NaI in THF at 80 degrees 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 reaction mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.
Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones / Ghelfi, Franco; G., Ghirardini; Libertini, Emanuela; Forti, Luca; Pagnoni, Ugo Maria. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 40:(1999), pp. 8595-8597. [10.1016/S0040-4039(99)01798-0]
Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones
GHELFI, Franco;LIBERTINI, Emanuela;FORTI, Luca;PAGNONI, Ugo Maria
1999
Abstract
3-Benzylimino-2-pyrrolidinones can be prepared in good yield by heating 3-chloro-4-chloromethyl-2-pyrrolidinones, benzylamine and NaI in THF at 80 degrees 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 reaction mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.
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