Pd-catalyzed amination of nucleoside arylsulfonates to yield N6-aryl-2,6-diaminopurine nucleosides

被引：52

作者：

Gunda, P

Russon, LM

Lakshman, MK

机构：

[1] CUNY City Coll, Dept Chem, New York, NY 10031 USA

[2] Analyt Branford Inc, Branford, CT 06405 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 46期

关键词：

amination; C-C coupling; nucleosides; palladium; phosphane ligands;

D O I：

10.1002/anie.200460782

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical equation presented). Substituents on both the nucleoside arylsulfonate as well as the aryl amine component have a significant impact on their coupling to form 2,6-diaminopurine-2′-deoxyribonucleosides (see scheme). A systematic study of ligands for the Pd catalysts in amination and C-C cross-coupling reactions gives insight into the structural elements that lead to effective catalysis.

引用

页码：6372 / 6377

页数：6

共 47 条

[1] A chemical method for site-specific modification of RNA: The convertible nucleoside approach
Allerson, CR
Chen, SL
Verdine, GL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) : 7423 - 7433
[2] Synthesis of biologically active N2-amine adducts of 2′-deoxyguanosine
Bonala, RR
Shishkina, IG
Johnson, F
[J]. TETRAHEDRON LETTERS, 2000, 41 (38) : 7281 - 7284
[3] ACYLATION OF 2',3',5'-TRI-O-ACETYLGUANOSINE
BRIDSON, PK
MARKIEWICZ, WT
REESE, CB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (21) : 791 - 792
[4] Synthesis of N2 2′-deoxyguanosine adducts formed by 1-nitropyrene
Chakraborti, D
Colis, L
Schneider, R
Basu, AK
[J]. ORGANIC LETTERS, 2003, 5 (16) : 2861 - 2864
[5] NEW GUANOSINE DERIVATIVES - FACILE O-6-PHOSPHORYLATION, THIOPHOSPHINYLATION SULFONYLATION AND SILYLATION OF GUANOSINE DERIVATIVES BY 4-DIMETHYLAMINOPYRIDINE CATALIZED REACTION
DASKALOV, HP
SEKINE, M
HATA, T
[J]. TETRAHEDRON LETTERS, 1980, 21 (40) : 3899 - 3902
[6] Chemical synthesis of cross-linked purine nucleosides
De Riccardis, F
Johnson, F
[J]. ORGANIC LETTERS, 2000, 2 (03) : 293 - 295
[7] A general method for the synthesis of the N2- and N6- carcinogenic amine adducts of 2′-deoxyguanosine and 2′-deoxyadenosine
De Riccardis, F
Bonala, RR
Johnson, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (45) : 10453 - 10460
[8] Hydroxycarbonylation of styrene with palladium catalysts The influence of the mono- and bidentate phosphorus ligand
del Río, I
Ruiz, N
Claver, C
van der Veen, LA
van Leeuwen, PWNM
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 161 (1-2) : 39 - 48
[9] Frost CG, 1998, J CHEM SOC PERK T 1, P2615
[10] SYNTHESIS OF O-6-ALKYLATED DEOXYGUANOSINE NUCLEOSIDES
GAFFNEY, BL
JONES, RA
[J]. TETRAHEDRON LETTERS, 1982, 23 (22) : 2253 - 2256

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