SNAr iodination of 6-chloropurine nucleosides: aromatic Finkelstein reactions at temperatures below -40 degrees C.
Mesitoyl or toluoyl esters of inosine and 2'-deoxyinosine were deoxychlorinated at C6 to give the crystalline 6-chloropurine nucleoside derivatives, which underwent quantitative conversion to the 6-iodo analogues with NaI/TFA/butanone at -50 to -40 degrees C. The 6-iodo compounds were efficient substrates for SNAr, Sonogashira, and Suzuki-Miyaura reactions, in contrast with the 6-chloro analogues, and gave good to high yields of C-N and C-C coupled products.
Liu
Jiangqiong
J
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Janeba
Zlatko
Z
Robins
Morris J
MJ
D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013696:Temperature
D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D011684:Purine Nucleosides