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    A new and concise route towards xanthines through a double-amidination reaction is described; consecutive intermolecular C-Cl and intramolecular oxidative C-H amidination. N-uracil amidines are obtained through SN AE on a 6-chlorouracil with amidines. Direct Cu-catalyzed oxidative C-H amidination on these N-uracil amidines yields polysubstituted xanthines. Sustainable oxidants, tBu2 O2 or O2 , can be used in this oxidase-type reaction. The protocol allows for the introduction of N1, N3, N7, and C8 substituents during the xanthine-scaffold construction, thus avoiding post-functionalization steps. Both 6-chlorouracils and amidines are readily available commercially or through synthesis. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.


    Bénédicte Morel, Philippe Franck, Johan Bidange, Sergey Sergeyev, Dan A Smith, Jonathan D Moseley, Bert U W Maes. Concise Xanthine Synthesis through a Double-Amidination Reaction of a 6-Chlorouracil with Amidines using Base-Metal Catalysis. ChemSusChem. 2017 Feb 08;10(3):624-628

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    PMID: 27899009

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