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

[11] Preparation of C8-amine and acetylamine adducts of 2′-deoxyguanosine suitably protected for DNA synthesis
Gillet, LCJ
Schärer, OD
[J]. ORGANIC LETTERS, 2002, 4 (24) : 4205 - 4208
[12] Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides
Hartwig, JF
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) : 852 - 860
[13] HARTWIG JF, 2000, MODERN AMINATION MET, P195
[14] Chemical synthesis of cross-link lesions found in nitrous acid treated DNA:: A general method for the preparation of N2-substituted 2′-deoxyguanosines
Harwood, EA
Hopkins, PB
Sigurdsson, ST
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 2959 - 2964
[15] Chemical synthesis and preliminary structural characterization of a nitrous acid interstrand cross-linked duplex DNA
Harwood, EA
Sigurdsson, ST
Edfeldt, NBF
Reid, BR
Hopkins, PB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5081 - 5082
[16] Havelková M, 1999, SYNLETT, P1145
[17] Havelková M, 2001, SYNTHESIS-STUTTGART, P1704
[18] O-ALLYL PROTECTION OF GUANINE AND THYMINE RESIDUES IN OLIGODEOXYRIBONUCLEOTIDES
HAYAKAWA, Y
HIROSE, M
NOYORI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) : 5551 - 5555
[19] 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
Hocek, M
Holy, A
Votruba, I
Dvoráková, H
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (09) : 1817 - 1825
[20] Cytostatic 6-arylpurine nucleosides III.: Synthesis and structure-activity relationship study in cytostatic activity of 6-aryl-, 6-hetaryl- and 6-benzylpurine ribonucleosides
Hocek, M
Holy, A
Votruba, I
Dvorákova, H
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2001, 66 (03) : 483 - 499

← 1 2 3 4 5 →