NDLI: Synthesis of 4-Aminoquinazolines by Palladium-Catalyzed Intramolecular Imidoylation of N-(2-Bromoaryl)amidines

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Rýcek, Lukás De Kanter, Frans J. J. Ruijter, Eelco Sergeyev, Sergey Kuijer, Sander Orru, Romano V. A. Maes, Bert U. W. Van Baelen, Gitte Janssen, Elwin
Description	Author Affiliation: Van Baelen G ( Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.)
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.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	52
Volume Number	17
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2011-12-23
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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Synthesis of 4-Aminoquinazolines by Palladium-Catalyzed Intramolecular Imidoylation of N-(2-Bromoaryl)amidines