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Regioselective Direct C-H Arylations of Protected Uracils. Synthesis of 5- and 6-Aryluracil Bases

SYSNO ASEP	0361006
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Regioselective Direct C-H Arylations of Protected Uracils. Synthesis of 5- and 6-Aryluracil Bases
Author(s)	Čerňová, Miroslava (UOCHB-X) Čerňa, Igor (UOCHB-X) Pohl, Radek (UOCHB-X)_{RID, ORCID} Hocek, Michal (UOCHB-X)_{RID, ORCID}
Number of authors	4
Source Title	Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263 Roč. 76, č. 13 (2011), s. 5309-5319
Number of pages	11 s.
Language	eng - English
Country	US - United States
Keywords	pyrimidines ; uracil ; direct C-H arylations ; palladium
Subject RIV	CC - Organic Chemistry
R&D Projects	LC06077 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000291920900016
DOI	10.1021/jo2006494
Annotation	A new regioselective synthesis of 5- and 6-aryluracil bases has been developed based on direct C-H arylations of diverse 1,3-protected uracils. Benzyl-protected uracils were selected as the most practical in terms of stability during the arylation and facile cleavage of the benzyl groups. Pd-catalyzed C-H arylations in absence of CuI gave preferentially 5-aryl-, whereas the reactions in presence of CuI gave 6-aryl-1,3-dibenzyluracils. Final deprotection either by transfer hydrogenolysis over Pd/C or by treatment with BBr3 gave the desired free arylated uracil bases in good yields.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2012

Number of the records: 1