Perfluoroalkylation of 6-iodopurines by trimethyl(perfluoroalkyl)silanes. Synthesis of 6-(perfluoroalkyl)purine bases, nucleosides and acyclic nucleotide analogues

被引:36
作者
Hocek, M [1 ]
Holy, A [1 ]
机构
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic
关键词
purines; nucleosides; cross-coupling reactions; trifluoromethylation; perfluoroalkylation; cuprates; fluorinated compounds; cytostatic activity;
D O I
10.1135/cccc19990229
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A CuI/KF mediated perfluoroalkylation reaction of various 9-substituted 6-iodopurines 1 with trimethyl(trifluoromethyl)silane or heptafluoropropyl(trimethyl)silane was used for the synthesis of the corresponding 6-(trifluoromethyl)- and 6-(heptafluoropropyl)purine derivatives (purine bases, nucleosides and acyclic nucleotide analogues) in moderate to good yields.
引用
收藏
页码:229 / 241
页数:13
相关论文
共 51 条
[1]   PURINE STUDIES .4. A SEARCH FOR COVALENT HYDRATION IN 8-SUBSTITUTED PURINES [J].
ALBERT, A .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (05) :438-&
[2]   ACYLATION OF NITROGEN HETEROCYCLES .2. CARBOBENZOXYLATION OF SUBSTITUTED ADENINES UNDER CONDITIONS OF SCHOTTEN-BAUMANN REACTION [J].
ALTMAN, J ;
BENISHAI, D .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (05) :679-&
[3]  
ANDREL G, UNPUB
[4]   REGIOSELECTIVE COUPLING OF TETRAALKYLAMMONIUM SALTS OF 6-IODO-2-AMINOPURINE TO A CYCLOBUTYL TRIFLATE - EFFICIENT PREPARATION OF HOMOCHIRAL BMS-180,194, A POTENT ANTIVIRAL CARBOCYCLIC NUCLEOSIDE [J].
BISACCHI, GS ;
SINGH, J ;
GODFREY, JD ;
KISSICK, TP ;
MITT, T ;
MALLEY, MF ;
DIMARCO, JD ;
GOUGOUTAS, JZ ;
MUELLER, RH ;
ZAHLER, R .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2902-2905
[5]   9-benzyladenines: Potent and selective cAMP phosphodiesterase inhibitors [J].
Bourguignon, JJ ;
Desaubry, L ;
Raboisson, P ;
Wermuth, CG ;
Lugnier, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (12) :1768-1770
[6]  
CHEA MY, 1995, J MED CHEM, V38, P359
[7]   POLYFLUOROALKYLATION OF BROMOHETEROCYCLIC COMPOUNDS VIA PERFLUOROALKYLCOPPER INTERMEDIATES [J].
CHEN, GJ ;
TAMBORSKI, C .
JOURNAL OF FLUORINE CHEMISTRY, 1990, 46 (01) :137-159
[8]   POLYFLUOROALKYLATION OF BROMOAROMATIC COMPOUNDS VIA PERFLUOROALKYLCOPPER INTERMEDIATES [J].
CHEN, GJ ;
TAMBORSKI, C .
JOURNAL OF FLUORINE CHEMISTRY, 1989, 43 (02) :207-228
[9]  
Duschinsky R., 1957, J AM CHEM SOC, V79, P494
[10]   Synthesis of acyclic nucleotide analogues derived from 6-(sec- or tert-alkyl)purines via coupling of 6-chloropurine derivatives with organocuprates [J].
Dvoráková, H ;
Dvorák, D ;
Holy, A .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1998, 63 (12) :2065-2074