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Concise xanthine synthesis through a double-amidination reaction of a 6-chlorouracil with amidines using base-metal catalysis

Tijdschriftbijdrage - Tijdschriftartikel

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.
Tijdschrift: Chemsuschem
ISSN: 1864-5631
Volume: 10
Pagina's: 624 - 628
Jaar van publicatie:2017
Trefwoorden:A1 Journal article
BOF-publication weight:3
CSS-citation score:1
Authors from:Higher Education