期刊
CHEMSUSCHEM
卷 10, 期 3, 页码 624-628出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201601483
关键词
amidination; base metal; cross-dehydrogenative; reaction; oxidative C-H amination; xanthines
资金
- Innovative Medicines Initiative [115360]
- European Union's Seventh Framework Programme (FP7)
- COST (European Cooperation in Science and Technology)
- Fund for Scientific Research (FWO-Flanders)
- Hercules foundation
- NSF [1337296, 0087210]
- Ohio Board of Regents Grant [CAP-491]
- Youngstown State University
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, tBu(2)O(2) or O-2, 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.
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