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Synthesis 2011(18): 3027-3031  
DOI: 10.1055/s-0030-1260125
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

The Aldol Addition of Readily Enolizable 1,3-Dicarbonyl Compounds to 2-Cyanobenzaldehyde in the Synthesis of Novel 3-Substituted Isoindolinones

Vijaykumar Moreb, Antonia Di Molab, Milena Perilloa, Paolo De Caprariisb, Rosanna Filosab, Antonella Pedutob, Antonio Massa*a
Dipartimento di Chimica e Biologia, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy
Fax: +39(89)969603; e-Mail: amassa@unisa.it;
Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy
Further Information

Publication History

Received 3 May 2011
Publication Date:
01 August 2011 (online)

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Abstract

The aldol addition of readily enolizable 1,3-dicarbonyl compounds to 2-cyanobenzaldehyde in the presence of a tertiary amine led to a series of new 3-substituted isoindolinones. Despite the instability of the related aldols, this synthesis was possible because of the intramolecular trapping of the adducts with the cyano group due to a tandem process of cyclization and rearrangement. Simple decarboxylation of some derivatives gave access to very useful compounds.

Key words

isoindolinones - aldol addition - enolizable 1,3-dicarbonyl compounds - 2-cyanobenzaldehyde

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