Copper catalyzed arylation with boronic acids for the synthesis of N1-aryl purine nucleosides

被引：22

作者：

Strouse, JJ

Jeselnik, M

Tapaha, F

Jonsson, CB

Parker, WB

Arterburn, JB

机构：

[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA

[2] So Res Inst, Birmingham, AL 35205 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 34期

关键词：

copper; coupling; heteroatom; nucleoside;

D O I：

10.1016/j.tetlet.2005.06.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of N-1-aryl inosine and guanosine derivatives is described. The procedure for chemoselective N-1-arylation involves the mild oxidative copper(II) mediated coupling with boronic acids. This approach provides access to substituted N-1-aryl purines with interesting structural characteristics and novel scaffolds for drug discovery. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5699 / 5702

页数：4

相关论文

共 27 条

[1] Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II) [J].

Bakkestuen, AK ;

Gundersen, LL .

TETRAHEDRON LETTERS, 2003, 44 (16) :3359-3362

[2] Unnatural ligands for engineered proteins: New tools for chemical genetics [J].

Bishop, A ;

Buzko, O ;

Heyeck-Dumas, S ;

Jung, I ;

Kraybill, B ;

Liu, Y ;

Shah, K ;

Ulrich, S ;

Witucki, L ;

Yang, F ;

Zhang, C ;

Shokat, KM .

ANNUAL REVIEW OF BIOPHYSICS AND BIOMOLECULAR STRUCTURE, 2000, 29 :577-606

[3] Synthesis of 6-alkenyl- and 6-alkynylpurines with cytokinin activity [J].

Bråthe, A ;

Gundersen, LL ;

Rise, E ;

Eriksen, AB ;

Vollsnes, AV ;

Wang, LN .

TETRAHEDRON, 1999, 55 (01) :211-228

[4] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[5] Synthesis of oligonucleotides containing bulky adducts at guanine N2 via the phosphoramidite of O2-triflate-O6-NPE 2′-deoxyxanthosine [J].

Cooper, MD ;

Hodge, RP ;

Tamura, PJ ;

Wilkinson, AS ;

Harris, CM ;

Harris, TM .

TETRAHEDRON LETTERS, 2000, 41 (19) :3555-3558

[6] Highlights in the Development of New Antiviral Agents [J].

De Clercq, E. .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2002, 2 (02) :163-175

[7]

DENAPOLI L, 1995, J ORG CHEM, V60, P2251

[8] Expanding the diversity of purine libraries [J].

Ding, S ;

Gray, NS ;

Ding, Q ;

Schultz, PG .

TETRAHEDRON LETTERS, 2001, 42 (50) :8751-8755

[9] Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].

Evans, DA ;

Katz, JL ;

West, TR .

TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940

[10] Nucleic acid related compounds.: 116.: Nonaqueous diazotization of aminopurine nucleosides.: Mechanistic considerations and efficient procedures with tert-butyl nitrite or sodium nitrite [J].

Francom, P ;

Janeba, Z ;

Shibuya, S ;

Robins, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19) :6788-6796