Complementary Synthetic Approaches
to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application
to the Synthesis of Falipamil and 5-HT1A Receptor Ligand
Analogues

Magali Lorion; Axel Couture; Eric Deniau; Pierre Grandclaudon

doi:10.1055/s-0028-1088048

PAPER

Complementary Synthetic Approaches to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application to the Synthesis of Falipamil and 5-HT_1A Receptor Ligand Analogues

Magali Lorion^a,b, Axel Couture*^a,b, Eric Deniau^a,b, Pierre Grandclaudon^a,b
^a LCOP, Université des Sciences et Technologies de Lille 1, Bâtiment C3(2), 59655 Villeneuve d’Ascq, France
Fax: +33(3)20336309; e-Mail: axel.couture@univ-lille1.fr;
^b CNRS, UMR 8009 ‘Chimie Organique et Macromoléculaire’, 59655 Villeneuve d’Ascq, France

Abstract

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Abstract

Different synthetic approaches for the elaboration of poly and diversely substituted isoindolinones tailed with constitutionally diverse aminoalkylated chains have been developed. The key step is based upon the preliminary assembly of the isoindolinone template equipped with hydroxyalkyl appendages. Subsequent manipulation of the terminal hydroxy functionality afforded the targeted compounds and the synthetic utility of these approaches has been emphasized by the synthesis of the bradycardic agent falipamil and 5-HT_1A receptor ligand analogues.

Key words

carbanions - metalation - lactams - ring closure - ring opening

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References

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Complementary Synthetic Approaches to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application to the Synthesis of Falipamil and 5-HT1A Receptor Ligand Analogues

Complementary Synthetic Approaches to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application to the Synthesis of Falipamil and 5-HT_1A Receptor Ligand Analogues