872002-68-1Relevant academic research and scientific papers
Synthesis of 4-aminoquinazolines by palladium-catalyzed intramolecular imidoylation of N-(2-bromoaryl)amidines
Van Baelen, Gitte,Kuijer, Sander,Rycek, Lukas,Sergeyev, Sergey,Janssen, Elwin,De Kanter, Frans J. J.,Maes, Bert U. W.,Ruijter, Eelco,Orru, Romano V. A.
, p. 15039 - 15044 (2011)
Compared with the widespread use of carbonylative Pd-catalyzed cross-coupling reactions, similar reactions involving isocyanide insertion are almost virgin territory. We investigated the intramolecular imidoylative cross-coupling of N-(2-bromoaryl)amidines, leading to 4-aminoquinazolines. After thorough optimization of the reaction with respect to palladium source and loading, ligand, base, temperature, and solvent, a small library of 4-aminoquinazolines was prepared to determine the scope of this method. Various substituents are tolerated on the amidine and the isocyanide, providing efficient access to a broad range of diversely substituted 4-aminoquinazolines of significant pharmaceutical interest.
