Synthesis of Nitro N,N′-Dipyridinylamines via Oxidative Nucleophilic Substitution of Hydrogen

Oana-Irina Patriciu; Christelle Pillard; Adriana-LuminiŢa Fînaru; Ioan Sãndulescu; Gérald Guillaumet

doi:10.1055/s-2007-990896

PAPER

Synthesis of Nitro N,N′-Dipyridinylamines via Oxidative Nucleophilic Substitution of Hydrogen

Oana-Irina Patriciu^a,b,c, Christelle Pillard^a, Adriana-LuminiŢa Fînaru^b, Ioan Sãndulescu^c, Gérald Guillaumet*^a
^a Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans, Cedex 2, France
Fax: +33(2)38417281; e-Mail: gerald.guillaumet@univ-orleans.fr;
^b Laboratorul de Sintezã Bio-organicã ºi Analizã Structuralã, Universitatea Bacãu, 157 Calea Mãrãºeºti, 600115 Bacãu, Romania
^c Catedra de Tehnologie Chimicã ºi Catalizã, Facultatea de Chimie, Universitatea Bucureºti, Bd. Regina Elisabeta Nr. 4-12, 030018 Bucureºti, Romania

Abstract

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Abstract

The amination of 3-nitropyridines with aromatic amides generated from various aminopyridine derivatives proceeded unexpectedly in the position para to the nitro group, giving the oxidative nucleophilic substitution of hydrogen (ONSH) derived compounds. After optimization, this reaction allowed easy access to interesting 3-nitro-substituted N,N′-dipyridinylamines.

Key words

heterocycles - pyridines - amination - nucleophilic aromatic substitution - palladium

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