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

被引：53

作者：

Cernova, Miroslava ^{[1
]}

Cerna, Igor ^{[1
]}

Pohl, Radek ^{[1
]}

Hocek, Michal ^{[1
]}

机构：

[1] Acad Sci Czech Republic, Inst Organ Chem & Biochem, Gilead Sci & IOCB Res Ctr, Prague 6, Czech Republic

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 13期

关键词：

CATALYZED DIRECT ARYLATION; DIRECT C-5 ARYLATION; ENZYMATIC INCORPORATION; SUBSTITUTED URACILS; PALLADIUM; DERIVATIVES; HETEROCYCLES; 2,4(5)-DIARYL-1H-IMIDAZOLES; 4(5)-ARYL-1H-IMIDAZOLES; FUNCTIONALIZATION;

D O I：

10.1021/jo2006494

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new regioselective synthesis of 5- and 6-aryluracil bases based on direct C-H arylations of diverse 1,3-protected uracils has been developed. 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 the absence of CuI gave preferentially 5-aryl-, whereas the reactions in the presence of CuI gave 6-aryl-1,3-dibenzyluracils. Final deprotection either by transfer hydrogenolysis over Pd/C or by treatment with BBr(3) gave the desired free arylated uracil bases in good yields.

引用

页码：5309 / 5319

页数：11

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