33512-51-5Relevant articles and documents
Synthesis of 2'-deoxyisoinosine and related 2'-deoxyribonucleosides
Seela,Chen,Bindig,Kazimierczuk
, p. 194 - 202 (2007/10/02)
Various 2-substituted purine and pyrrolo[2,3-d]pyrimidine 2'-deoxyribonucleosides with methylthio (13a), chloro (13b), methoxy (9b), and oxo (2, 3) substituents at C(2) are prepared. They are obtained either via stereoselective nucleobase-anion glycosylation or by base transformation. A three-step synthesis of the unknown 2'-deoxyisoinosine (2) from 2'-deoxyguanosine (15) is described. Compound 2 as well as its 7-deazapurine derivative 3 exhibit strong fluorescence.
Occurrence of the SNANRORC Mechanism in the Amination of 2-Substituted Purines with Potassium Amide in Liquid Ammonia
Kos, Nico J.,Plas, Henk C. van der
, p. 2942 - 2945 (2007/10/02)
The reactions of 2-chloro-, 2-fluoro- and 2-(methylthio)purine with potassium amide in liquid ammonia lead to the formation of 2-aminopurine.When these reactions are carried out with 15N-labeled potassium amide, ring-labeled 2-aminopurine is found.This demonstrates that a ring opening occurs during the amination.Formation of an anionic ? adduct at position 6 is proven by low-temperature NMR spectroscopy, and evidence is obtained for the formation of an open-chain intermediate, although this intermediate could not be isolated in a pure state.Reaction of the open-chain intermediate with hydriodic acid gives the thus far unknown 2-iodopurine. 2-Chloro-6-phenylpurine also reacts via ring opening into 2-amino-6-phenylpurine.However, 2-chloro-6-methyl- and 2-chloro-6,8-di-tert-butylpurine are found to be unreactive.
