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

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

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...

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Veröffentlicht in:Synthesis (Stuttgart) 2006-08, Vol.2006 (16), p.2794-2798
Hauptverfasser: Begouin, Agathe, Hesse, Stéphanie, Queiroz, Maria-João R., Kirsch, Gilbert
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container_issue 16
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container_title Synthesis (Stuttgart)
container_volume 2006
creator Begouin, Agathe
Hesse, Stéphanie
Queiroz, Maria-João R.
Kirsch, Gilbert
description 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.
doi_str_mv 10.1055/s-2006-942510
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title Reactivity of Substituted Bromothiophenecarboxylates in Palladium-Catalyzed N-Arylation of Hetarylamines
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