Article

Facile Pd-catalyzed amination of imidazolin-1-yl chloroazines under microwave irradiation: Toward a new kinase-inhibitory chemotype

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Abstract

The imidazolin-1-yl azine moiety, constructed using a recently developed Buchwald–Hartwig-type arylation methodology, displays excellent chemical stability under subsequent microwave-assisted Pd-catalyzed amination with a range of N-nucleophiles. This finding extends the usage of imidazolin-1-yl azines for bioactive compound library design. The latter is exemplified herein by the discovery of micromolar kinase inhibitors.

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Chapter
Nitrogen-containing organic compounds, in particular, heterocycles are of high importance in numerous fields including the pharmaceutical and agrochemical industries. This review attempts to collect useful information with respect to the synthesis of nitrogen-containing compounds through the formation of CN bonds carried out under microwave irradiation. The two major fields covered are the synthesis of arylated and alkylated amines and varied ring-forming reactions. The latter part is organized in order of increasing complexity. The syntheses of simple monocyclic compounds with a single nitrogen atom through complex ring systems with numerous ring nitrogen atoms are discussed and analyzed. Detailed treatments of catalyzed and un-catalyzed processes illustrate the rich chemistry and the multitude of approaches available for the synthesis of nitrogen-containing compounds.
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