Download PDF
Synthesis 2006(16): 2794-2798  
DOI: 10.1055/s-2006-942510
PAPER
© Georg Thieme Verlag Stuttgart · New York

Reactivity of Substituted Bromothiophenecarboxylates in Palladium-Catalyzed N-Arylation of Hetarylamines

Agathe Begouina, Stéphanie Hessea, Maria-João R. P. Queirozb, Gilbert Kirsch*a
a Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, Université Paul-Verlaine Metz, 1 Boulevard Arago, 57078 METZ Technopôle, France
Fax: +33(3)87315801; e-Mail: kirsch@univ-metz.fr;
b Centro de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
Further Information

Publication History

Received 20 April 2006
Publication Date:
25 July 2006 (online)

    Permissions and Reprints All articles of this category

Abstract

The N-arylation of hetarylamines by reaction of aminopyridines or aminoquinolines with substituted bromothiophene-2- or -3-carboxylates is described. From 2-aminopyridines and 1-aminoisoquinoline, polycyclic compounds were obtained in one-pot, two-step reactions: C-N coupling is followed by intramolecular cyclization involving the nitrogen atom of the heterocyclic ring and the carboxylate. Steric hindrance seems to be a limitation for the latter reaction, because when 2-amino-6-picoline was used, the corresponding dihetarylamines were obtained.

Key words

palladium catalysis - amination - bromothiophenes - aminopyridines