Azoles as Suzuki cross-coupling leaving groups:: Syntheses of 6-arylpurine 2′-deoxynucleosides and nucleosides from 6-(imidazol-1-yl)- and 6-(1,2,4-triazol-4-yl)purine derivatives

被引:98
作者
Liu, JQ [1 ]
Robins, MJ [1 ]
机构
[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA
关键词
D O I
10.1021/ol048490d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
6-(Imidazol-1-yl)-, 6-(benzimidazol-1-yl)-, and 6-(1,2,4-triazol-4-yl)purine nucleosides undergo a nickel-mediated C-C cross-coupling of azole-substituted purine derivatives with arylboronic acids to give good yields of 6-arylpurine nucleosides.
引用
收藏
页码:3421 / 3423
页数:3
相关论文
共 25 条
[1]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[2]   The first Suzuki cross-couplings of aryltrimethylammonium salts [J].
Blakey, SB ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6046-6047
[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]   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
[5]   Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems [J].
Grasa, GA ;
Viciu, MS ;
Huang, JK ;
Zhang, CM ;
Trudell, ML ;
Nolan, SP .
ORGANOMETALLICS, 2002, 21 (14) :2866-2873
[6]  
Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO
[7]  
2-Y
[8]   Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides:: Application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids [J].
Hocek, M ;
Holy, A ;
Votruba, I ;
Dvoráková, H .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (09) :1817-1825
[9]   Cytostatic 6-arylpurine nucleosides II.: Synthesis of sugar-modified derivatives:: 9-(2-deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-deoxy-β-D-ribofuranosyl)- and 9-(2,3-dihydroxypropyl)-6-phenylpurines [J].
Hocek, M ;
Holy, A ;
Votruba, I ;
Dvoráková, H .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2000, 65 (11) :1683-1697
[10]  
HOCKE M, 2001, COLLECT CZECH CHEM C, V66, P483