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

被引:53
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
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
收藏
页码:6372 / 6377
页数:6
相关论文
共 47 条
[11]   Preparation of C8-amine and acetylamine adducts of 2′-deoxyguanosine suitably protected for DNA synthesis [J].
Gillet, LCJ ;
Schärer, OD .
ORGANIC LETTERS, 2002, 4 (24) :4205-4208
[12]   Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides [J].
Hartwig, JF .
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 [J].
Harwood, EA ;
Hopkins, PB ;
Sigurdsson, ST .
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 [J].
Harwood, EA ;
Sigurdsson, ST ;
Edfeldt, NBF ;
Reid, BR ;
Hopkins, PB .
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 [J].
HAYAKAWA, Y ;
HIROSE, M ;
NOYORI, R .
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 [J].
Hocek, M ;
Holy, A ;
Votruba, I ;
Dvoráková, H .
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 [J].
Hocek, M ;
Holy, A ;
Votruba, I ;
Dvorákova, H .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2001, 66 (03) :483-499