Synthesis of 4‐Aminoquinazolines by Palladium‐Catalyzed Intramolecular Imidoylation of  N ‐(2‐Bromoaryl)amidines | Zendy

Van Baelen Gitte | Zendy; Kuijer Sander | Zendy; Rýček Lukáš | Zendy; Sergeyev Sergey | Zendy; Janssen Elwin | Zendy; de Kanter Frans J. J. | Zendy; Maes Bert U. W. | Zendy; Ruijter Eelco | Zendy; Orru Romano V. A. | Zendy

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

Author(s) -

Van Baelen Gitte,

Kuijer Sander,

Rýček Lukáš,

Sergeyev Sergey,

Janssen Elwin,

de Kanter Frans J. J.,

Maes Bert U. W.,

Ruijter Eelco,

Orru Romano V. A.

Publication year - 2011

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201102468

Subject(s) - amidine , intramolecular force , isocyanide , palladium , ligand (biochemistry) , catalysis , chemistry , solvent , combinatorial chemistry , coupling reaction , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , receptor

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.

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