Synthesis of 4-aminoquinazolines by palladium-catalyzed intramolecular imidoylation of N-(2-bromoaryl)amidines

G.A.K. van Baelen, S. Kuijer, L. Rycek, S. Sergeyev, E. Janssen, F.J.J. de Kanter, B.U.W. Maes, E. Ruijter, R.V.A. Orru

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)15039-15044
Number of pages6
JournalChemistry: A European Journal
Volume17
Issue number52
Early online date28 Nov 2011
DOIs
Publication statusPublished - 23 Dec 2011

Fingerprint

Dive into the research topics of 'Synthesis of 4-aminoquinazolines by palladium-catalyzed intramolecular imidoylation of N-(2-bromoaryl)amidines'. Together they form a unique fingerprint.

Cite this