Dichotomy in regioselectivity of Pd-catalyzed direct C-H arylation of protected uracils

0361546 - ÚOCHB 2012 CZ eng C - Konferenční příspěvek (zahraniční konf.)
Čerňová, Miroslava - Hocek, Michal
Dichotomy in regioselectivity of Pd-catalyzed direct C-H arylation of protected uracils.
Chemistry of Nucleic Acid Components. 15th Symposium. Praha: Institute of Organic Chemistry and Biochemistry AS CR, v. v. i., 2011 - (Hocek, M.), s. 314-316. Collection Symposium Series, 12. ISBN 978-80-86241-37-1.
[Chemistry of Nucleic Acid Components /15./. Český Krumlov (CZ), 05.06.2011-10.06.2011]
Grant CEP: GA MŠMT(CZ) LC06077
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: direct C-H arylation * uracils * pyrimidines * palladium
Kód oboru RIV: CC - Organická chemie

Uracil bases and nucleosides bearing aryl groups in positions 5 or 6 are an important class of compounds and display wide range of biological activities1. In addition, arylation in position 5 is often used for labeling of nucleotides, oligonucleotides and DNA for applications in bioanalysis or chemical biology2. The 5- or 6-aryluracils can be prepared by heterocyclization or by cross-coupling reactions of halouracils with arylboronic acids or stannanes or metallated uracils with aryl halides. Direct C–H arylation of uracil is an alternative to classical cross-couplings where the preparation of reactive organometallic reagent is avoided. Recently, we have developed regioselective Pd-catalyzed and/or Cu-mediated direct C–H arylations of 1,3-dimethyluracil as a model compound for pyrimidine bases to position C-5 or C-6 3.
Trvalý link: http://hdl.handle.net/11104/0198838