Cobalt‐catalyzed annulation of benzimidates or NH‐benzaldimines with ynamides: synthesis of 1‐alkoxy‐ and 1‐alkyl‐3‐aminoisoquinolines - Archive ouverte HAL
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2024

Cobalt‐catalyzed annulation of benzimidates or NH‐benzaldimines with ynamides: synthesis of 1‐alkoxy‐ and 1‐alkyl‐3‐aminoisoquinolines

Résumé

Inexpensive cobalt-catalyzed, pivalic acid-assisted oxidative CH functionalization of benzimidates or NH-benzaldimines with ynamides is presented, providing an access to novel 3-amino-isoquinoline derivatives. The procedure is compatible with various substrates featuring alkyl, alkoxy, acyl or halogen as substituents, heteroaryl structures, and diverse ynamides. Notably, the reaction has been successfully 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.

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Chimie organique
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hal-04578464 , version 1 (02-09-2024)

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Hamdi Sanaa, Liliane Mimoun, Pascal Retailleau, Elsa Anselmi, Cyril Nicolas, et al.. Cobalt‐catalyzed annulation of benzimidates or NH‐benzaldimines with ynamides: synthesis of 1‐alkoxy‐ and 1‐alkyl‐3‐aminoisoquinolines. Advanced Synthesis and Catalysis, 2024, 366, pp.2495-2500. ⟨10.1002/adsc.202400166⟩. ⟨hal-04578464⟩
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