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

收藏

页码：5309 / 5319

页数：11

相关论文

共 51 条

[21] A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds [J].

Do, Hien-Ouang ;

Khan, Rana M. Kashif ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :15185-15192

[22] Regioselective (site-selective) functionalisation of unsaturated halogenated nitrogen, oxygen and sulfur heterocycles by Pd-catalysed cross-couplings and direct arylation processes [J].

Fairlamb, Ian J. S. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1036-1045

[23]

FARINA V, 1991, SYNLETT, P157

[24] Synthesis of 1-[cis-3-(hydroxymethyl)cyclobutyl]-uracil, -thymine and -cytosine [J].

Frieden, M ;

Giraud, M ;

Reese, CB ;

Song, QL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17) :2827-2832

[25] Analysis of the concerted metalation-deprotonation mechanism in palladium-catalyzed direct arylation across a broad range of aromatic substrates [J].

Gorelsky, Serge I. ;

Lapointe, David ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (33) :10848-+

[26] Site-Selective Azaindole Arylation at the Azine and Azole Rings via N-Oxide Activation [J].

Huestis, Malcolm P. ;

Fagnou, Keith .

ORGANIC LETTERS, 2009, 11 (06) :1357-1360

[27] Researches on pyrimidines LXXIV Synthesis of 4-phenylcytosine [J].

Johnson, TB ;

Hemingway, EH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1915, 37 :378-383

[28] REMOVAL OF N-BENZYLOXYMETHYL AND N-BENZYLOXYMETHYL SUBSTITUENTS FROM SUBSTITUTED URACILS WITH BORON TRIBROMIDE [J].

KUNDU, NG ;

HERTZBERG, RP ;

HANNON, SJ .

TETRAHEDRON LETTERS, 1980, 21 (12) :1109-1112

[29] Switchable catalysis: Modular synthesis of functionalized pyrimidinones via selective sulfide and halide cross-coupling chemistry [J].

Kusturin, C ;

Liebeskind, LS ;

Rahman, H ;

Sample, K ;

Schweitzer, B ;

Srogl, J ;

Neumann, WL .

ORGANIC LETTERS, 2003, 5 (23) :4349-4352

[30] Improved chemical syntheses of 5,6-dihydro-5-fluorouracil [J].

LaFrate, Andrew L. ;

Katzenellenbogen, John A. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8573-8576

← 1 2 3 4 5 6 →