Details

Autor(en) / Beteiligte

• Morel, Bénédicte
• Franck, Philippe
• Bidange, Johan
• Sergeyev, Sergey
• Smith, Dan A.
• Moseley, Jonathan D.
• Maes, Bert U. W.

Titel

Concise Xanthine Synthesis through a Double‐Amidination Reaction of a 6‐Chlorouracil with Amidines using Base‐Metal Catalysis

Ist Teil von

• ChemSusChem, 2017-02, Vol.10 (3), p.624-628

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2017

Quelle

Wiley-Blackwell Journals

Beschreibungen/Notizen

• 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 SNAE on a 6‐chlorouracil with amidines. Direct Cu‐catalyzed oxidative C−H amidination on these N‐uracil amidines yields polysubstituted xanthines. Sustainable oxidants, tBu2O2 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. Simple xanthine synthesis: A new two‐step approach for the synthesis of polysubstituted xanthines is described. Starting from simple building blocks, 6‐chlorouracil and amidines, a SNAE amidination reaction is developed, followed by a base‐metal‐catalyzed intramolecular direct oxidative amidination. O2 or tBu2O2 can be used as oxidant for the latter transformation.