Cobalt‐Catalyzed Annulation of Benzimidates or NH‐Benzaldimines with Ynamides: Synthesis of 1‐Alkoxy‐ and 1‐Alkyl‐3‐Aminoisoquinolines

Cobalt‐Catalyzed Annulation of Benzimidates or NH‐Benzaldimines with Ynamides: Synthesis of 1‐Alkoxy‐ and 1‐Alkyl‐3‐Aminoisoquinolines

Inexpensive cobalt‐catalyzed, pivalic acid‐assisted oxidative C−H functionalization of benzimidates or NH‐benzaldimines with ynamides is presented, providing an access to 3‐aminoisoquinoline derivatives. The procedure is compatible with various substrates featuring alkyl, alkoxy, acyl or halogen as...

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Veröffentlicht in:Advanced synthesis & catalysis 2024-06, Vol.366 (11), p.2495-2500
Hauptverfasser: Sanaa, Hamdi, Mimoun, Liliane, Retailleau, Pascal, Anselmi, Elsa, Nicolas, Cyril, Gillaizeau, Isabelle
Format: Artikel
Sprache:eng
Schlagworte:
3-Aminoisoquinoline
Benzimidate
Chemical reactions
Chemical Sciences
Cobalt catalysis
C−H Activation/Annulation Reaction
Organic chemistry
Regioselectivity
Substrates
Ynamide
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container_end_page 2500
container_issue 11
container_start_page 2495
container_title Advanced synthesis & catalysis
container_volume 366
creator Sanaa, Hamdi
Mimoun, Liliane
Retailleau, Pascal
Anselmi, Elsa
Nicolas, Cyril
Gillaizeau, Isabelle
description Inexpensive cobalt‐catalyzed, pivalic acid‐assisted oxidative C−H functionalization of benzimidates or NH‐benzaldimines with ynamides is presented, providing an access to 3‐aminoisoquinoline derivatives. The procedure is compatible with various substrates featuring alkyl, alkoxy, acyl or halogen as substituents, heteroaryl structures, and diverse ynamides. The reaction has been scaled up, with subsequent transformation of the yielded products. Control experiments and mechanistic investigations corroborate the regioselectivity of this conversion, positioning the amine group proximal to the nitrogen atom in isoquinolines.
doi_str_mv 10.1002/adsc.202400166
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subjects 3-Aminoisoquinoline
Benzimidate
Chemical reactions
Chemical Sciences
Cobalt catalysis
C−H Activation/Annulation Reaction
Organic chemistry
Regioselectivity
Substrates
Ynamide
title Cobalt‐Catalyzed Annulation of Benzimidates or NH‐Benzaldimines with Ynamides: Synthesis of 1‐Alkoxy‐ and 1‐Alkyl‐3‐Aminoisoquinolines
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