Abstract
Synthesis of new N-norbornylimide substituted amide derivatives, their reductive Heck and domino Heck reactions
Highlights
Carboxamide functions are widely found in various molecules such as drugs, polymers, pharmaceutical agents, peptides, natural molecules, proteins, alkaloids, etc.[1]
The Kaufmann reductive Heck procedure could allow the palladium-catalyzed, stereoselective transformation of N-substituted tricyclic imides providing a new access to exo-aryl(hetaryl)-substituted tricyclic imides in the presence of triphenylarsine as a ligand.[24,25,26]. Having this information in mind, we focused on the synthesis of a new class of compounds including exoaryl(hetaryl)-substituted norbornylimide derivatives of N-4-azabicyclo[2.2.1]hept-8-ene-3-endo,5-endodicarboximide-4-yl-2-(4-azabicyclo[2.2.1]hept-8-ene-3-endo,5-endo-dicarboximide-4-yl)-3-methylpentanamide (5)
From the results presented in Scheme 6 it is apparent that the more reactive alkene is the one in the norbornene system proximal to the N,N-succinoylhydrazide functionality since the product composition 6a and 7a indicates that the bis-arylation succeeds the mono-arylation at the more reactive double bond
Summary
Carboxamide functions are widely found in various molecules such as drugs, polymers, pharmaceutical agents, peptides, natural molecules, proteins, alkaloids, etc.[1].
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