5-Amino-2-furylmethylamines - Appealing
Precursors of Amino­isoindolinones?

Raouf Medimagh; Sylvain Marque; Damien Prim; Saber Chatti

doi:10.1055/s-0029-1218614

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Synthesis 2010(5): 770-774
DOI: 10.1055/s-0029-1218614

PAPER

5-Amino-2-furylmethylamines - Appealing Precursors of Aminoisoindolinones?

Raouf Medimagh^a, Sylvain Marque*^a, Damien Prim^a, Saber Chatti^b
^a Université de Versailles Saint-Quentin-en-Yvelines, Institut Lavoisier de Versailles (ILV) UMR 8180, 45 Avenue des Etats-Unis, 78035 Versailles Cedex, France
Fax: +33(1)39254452; e-Mail: sylvain.marque@chimie.uvsq.fr;
^b Institut National de Recherche et d’Analyse Physicochimique (INRAP), Pôle Technologique de Sidi Thabet, 2020 Sidi Thabet, Tunisia

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Publication History

Received 4 November 2009
Publication Date:
16 December 2009 (online)

Abstract
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Abstract

Isoindolinones were constructed according to an original [4+2]-cycloaddition strategy. Unprecedented 5-amino-2-furylmethylamines were prepared and revealed as efficient precursors of new aminoisoindolinones, obtained via a Diels-Alder and lactamization sequence.

Key words

Diels-Alder reactions - furans - isoindolinones - multicomponent reactions

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14

A sequence involving the reaction between 1 and 2 prior to the successive addition of NaBH₄ and then 5 was first envisaged, but did not succeed; the sequence between 1 and 2, then 5, prior to the addition of NaBH₄ gave a mixture of products.