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Palladium(0)-Catalyzed Carbonylative One-Pot Synthesis of N-Acylguanidines

Linda Åkerbladh, Luke S. Schembri, Mats Larhed and Luke R. Odell*

*Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University, P.O. Box 574, SE-751 23 Uppsala, Sweden, Email: luke.odellorgfarm.uu.se

L. Åkerbladh, L. S. Schembri, M. Larhed, L. R. Odell, J. Org. Chem., 2017, 82, 12520-12529.

DOI: 10.1021/acs.joc.7b02294 (free Supporting Information)



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Abstract

A one-pot multicomponent carbonylation/amination sequence enables a convenient synthesis of N-acylguanidines. A formation of an N-cyanobenzamide intermediate from the Pd(0)-catalyzed carbonylative coupling of cyanamide and aryl iodides or bromides is followed by amination with various amines to provide the final N-acylguanidines in good yields. Furthermore, various heterocycles were prepared from the N-acylguanidines.

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Key Words

aminocarbonylation, amination


ID: J42-Y2017