Synthesis of 3-EWG-Substituted 2-Amino-5-hydroxyindoles via Nenitzescu Reaction

Jens Landwehr; Reinhard Troschütz

doi:10.1055/s-2005-872074

PAPER

Synthesis of 3-EWG-Substituted 2-Amino-5-hydroxyindoles via Nenitzescu Reaction

Jens Landwehr, Reinhard Troschütz*
Institut für Pharmazie und Lebensmittelchemie im Emil-Fischer-Centrum, Friedrich-Alexander-Universität, Schuhstr. 19, 91052 Erlangen, Germany
Fax: +49(9131)8522587; e-Mail: Troschuetz@pharmazie.uni-erlangen.de;

Abstract

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Abstract

A series of primary ketene aminals 2, substituted with an electron-withdrawing group were reacted with 1,4-benzoquinone (1) yielding new 3-EWG-substituted 2-amino-5-hydroxyindoles 3a-f. Treatment of ethyl 3,3-diaminoacrylate (2a) with naphthoquinone (20a) and heteroaromatic quinones 20b-d afforded [g]annulated 2-aminoindole-3-carboxylates 21a-d.

Key words

indoles - quinones - Michael reaction - nucleophilic addition - Nenitzescu reaction

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