155940-92-4Relevant academic research and scientific papers
Palladium-catalyzed ring-opening of cyclopropyl benzamides: Synthesis of benzo[c]azepine-1-ones via C(sp3)-H functionalization
Ladd, Carolyn L.,Roman, Daniela Sustac,Charette, André B.
supporting information, p. 4479 - 4487 (2013/06/26)
A variety of difficult to obtain benzo[c]azepine-1-ones are synthesized via a novel palladium-catalyzed, silver-promoted intramolecular cyclization of cyclopropyl benzamides. This biologically important class of molecules is prepared in an efficient and high-yielding manner from easily accessible starting materials. Both aryl bromides and iodides are effective substrates for the transformation. Mechanistic studies indicate that the reaction proceeds through a cyclopropyl C(sp3)-H cleavage step, followed by ring-opening, deprotonation, and reductive elimination.
Direct N-cyclopropylation of secondary acyclic amides promoted by copper
Racine, Emilie,Monnier, Florian,Vors, Jean-Pierre,Taillefer, Marc
supporting information, p. 7412 - 7414 (2013/09/23)
The N-cyclopropylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper system. The corresponding tertiary acyclic amides, which constitute a wide family of biologically active compounds, have been obtained in good to excellent yields.
