Mild and efficient functionalization at C6 of purine 2'-deoxynucleosides and ribonucleosides.
[reaction: see text] Treatment of sugar-protected inosine and 2'-deoxyinosine derivatives with a cyclic secondary amine or imidazole and I(2)/Ph(3)P/EtN(i-Pr)(2)/(CH(2)Cl(2) or toluene) gave quantitative conversions into 6-N-(substituted)purine nucleosides. S(N)Ar reactions with 6-(imidazol-1-yl) derivatives gave 6-(N, O, or S)-substituted products. The 6-(benzylsulfonyl) group underwent S(N)Ar displacement with an arylamine at ambient temperature.
Lin
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Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Robins
M J
MJ
D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D007202:Indicators and Reagents; D007288:Inosine / Q000031:analogs & derivatives / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
D003853:Deoxyribonucleosides; D007202:Indicators and Reagents; D011687:Purines; D012263:Ribonucleosides; D007288:Inosine; C012271:deoxyinosine