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Synthesis 2011(8): 1267-1278  
DOI: 10.1055/s-0030-1258478
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3-Alkyl-4-(chloromethyl)-1-RSO2-1H-pyrrol-2(5H)-ones, Using a Sequential ATRC/[1,2]-Elimination, from 2,2-Dichloro-N-(2-chloroallyl)-N-RSO2-amides

Matteo Bregolia, Fulvia Fellugab, Vincenzo Frennac, Franco Ghelfi*a, Ugo M. Pagnonia, Andrew F. Parsonsd, Giovanni Petrilloe, Domenico Spinellif
a Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, Via Campi 183, 41125 Modena, Italy
Fax: +39(59)373543; e-Mail: franco.ghelfi@unimore.it;
b Dipartimento di Scienze Chimiche, Università degli Studi di Trieste, Via Licio Giorgieri 1, 34127 Trieste, Italy
c Dipartimento di Chimica Organica ‘E.Paternò’, Università degli Studi di Palermo, Viale delle Scienze - Parco d’Orleans II, 90128 Palermo, Italy
d Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK
e Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Via Dodecaneso 31, 16146 Genova, Italy
f Dipartimento di Chimica ‘G. Ciamician’, Alma Mater Studiorum, Via Selmi 2, 40126 Bologna, Italy
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Publication History

Received 17 December 2010
Publication Date:
16 March 2011 (online)

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Abstract

The preparation of 3-alkyl-4-(chloromethyl)-1-RSO2-1H-pyrrol-2(5H)-ones was efficiently accomplished through a [1,2]-elimination of γ-lactams derived from the copper(I)-catalysed ATRC of 2,2-dichloro-N-(2-chloroallyl)-N-RSO2-amides. The two reactions can be integrated into a sequential one-pot process.

Key words

copper - cyclization - elimination - lactams - radical reaction

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A small configuration reversal, unexploitable in practical terms, operated at C3 by MeONa during the functional rearrangement of 3-chloro-4-(chloromethyl)-1-(pyridinyl)- and -1-[(2-pyrimidyl)methyl]pyrrolidin-2-one in MeONa/MeOH.8a