1681-15-8Relevant articles and documents
The synthesis of nebularine and its analogs via oxidative desulfuration in aqueous nitric acid
Xia, Ran,Sun, Li-Ping,Qu, Gui-Rong
, p. 88 - 91 (2016/12/24)
The synthesis of nebularine and its analogs has been achieved via oxidative desulfuration in H2O for the first time. With 50% HNO3as an oxidant and solvent, 18 products were obtained in good yields (70%–94%). The oxidative desulfuration system could tolerate different functional groups including fluoro, chloro, amino, alkyl, allyl, ribosyl, deoxyribosyl, and arabinofuranosyl groups.More importantly, the drug nebularine could be obtained successfully on a 20 g scale, which made this route more attractive for industrial applications.
Reduction of different electron-poor N-heteroarylhydrazines in strong basic conditions
Unciti-Broceta, Asier,Pineda De Las Infantas, Maria J.,Gallo, Miguel A.,Espinosa, Antonio
, p. 1754 - 1762 (2008/02/03)
The first application of the Wolff-Kishner reduction methodology to electron-poor heteroaromatic compounds is reported. Hydrazino-containing heterocycles with hydrazone-type tautomery have been reduced under basic conditions. This novel chemistry was successfully applied to mono-dehalogenate a number of electron-poor heterocycles in a regioselective manner. According to the experimental results, this reductive process is a base-catalyzed reaction that takes only place in the presence of air, probably through an oxygen-assisted mechanism. As consequence of the specific features of this kind of hydrazone/enehydrazine tautomers, the overall outcome of the process is the synthesis of a Shapirotype reduction product by simply using a milder version of the Huang-Minlon methodology.
Synthesis and properties of 2-guanidinopurines
Cesnek, Michal,Masojidkova, Milena,Holy, Antonin,Solinova, Veronika,Koval, Dusan,Kasicka, Vaclav
, p. 1303 - 1319 (2008/09/16)
2-Guanidinopurines were prepared as derivatives of 2,6-diamino-9-[2- (phosphonomethoxy)ethyl]-9H-purine (PMEDAP) (1), which shows an important antiviral activity. It completes earlier described synthesis of 6-guanidinopurine derivatives. The title compounds were obtained by the reaction of the corresponding 2-chloropurines with guanidine. 2- And 6-guanidinopurines were used as model compounds for determination of dissociation constants (pKa) of their ionogenic groups by capillary zone electrophoresis. The pKa values of ionogenic groups of the above compounds were compared with those of the corresponding aminopurines. The pKa of guanidino group at the purine moiety varies from 7.77 to 10.32. There is no protonation of N1-position in contrast to aminopurines. None of these compounds showed any antiviral activity.