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Synthesis of Quinazolin-4-ones by Copper-Catalyzed Isocyanide Insertion

JurriŽn W. Collet, Edith A. van der Nol, Tom R. Roose, Bert U. W. Maes, Eelco Ruijter and Romano V. A. Orru*

*Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ Amsterdam, The Netherlands, Email:

J. W. Collet, E. A. van der Nol, T. R. Roose, B. U. W. Maes, El Ruijter, R. V. A. Orru, J. Org. Chem., 2020, 85, 7378-7385.

DOI: 10.1021/acs.joc.0c00771

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A copper-catalyzed imidoylative cross-coupling/cyclocondensation reaction between 2-isocyanobenzoates and amines efficiently provides quinazolin-4-ones. The reaction utilizes Cu(II) acetate as an environmentally benign catalyst in combination with a mild base and proceeds well in anisole, a sustainable solvent. The use of aromatic amines as nucleophiles requires microwave heating.

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Key Words

quinazolin-4-ones, microwave synthesis

ID: J42-Y2020