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Silver Nitrate-Catalyzed Isocyanide Insertion/Lactamization Sequence to Imidazolones and Quinazolin-4-ones: Development and Application in Natural Product Synthesis

Antonin Clemenceau, Qian Wang and Jieping Zhu*

*Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland, Email:

A. Clemenceau, Q. Wang, J. Zhu, Org. Lett., 2017, 19, 4872-4875.

DOI: 10.1021/acs.orglett.7b02334

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Silver nitrate catalyzes a reaction of primary amines with methyl α,α-disubstituted α-isocyanoacetates to provide 3,5,5-trisubstituted imidazolones in very good yields via Ag-catalyzed insertion of the isocyano group into the N-H bond of the amine followed by in situ lactamization. The catalytic system also converts methyl 2-isocyanobenzoate and amines into quinazolin-4-ones in excellent yields.

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proposed mechanism

Total Syntheses of (±)-Evodiamine and Rutaecarpine

Key Words


ID: J54-Y2017