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Synlett 1993; 1993(1): 41-42
DOI: 10.1055/s-1993-22340
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Synthesis of Pyrroloisoquinolones via Organolithium Additions to N-Phenethylsuccinimides

Esther Lete* , Amagoia Egiarte, Nuria Sotomayor, Teresa Vicente, María-Jesús Villa
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad del País Vasco, Apdo. 644, E-48080 Bilbao, Spain
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Publication Date:
19 March 2002 (online)

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In the presence of n-butyl and t-butyllithium, N-phenethylsuccinimides undergo carbophilic addition to the carbonyl group previous to metal-hydrogen or metal-bromine exchange, while preferential aromatic metalation takes place on the iodinated imide. The cyclizations of the resulting organolithiums allow new and convenient entries to 8,9-dialkoxypyrrolo-[2,1-a]-isoquinolin-3(2H)-ones.