Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives

Jānis Miķelis Zaķis, Kaspars Ozols, Irina Novosjolova, Reinis Vilšķērsts, A Mishnev, Māris Turks

9-Substituted 2-chloro-6-sulfonylpurines provide 6-azido-2-sulfonylpurine derivatives with 61-83% yields when treated with sodium azide. Under optimized reaction conditions, the title compounds are obtained in a one-pot process, which involves a sequential treatment of 2,6-dichloropurines with a selected sodium sulfinate and sodium azide. Such a sulfonyl group dance (functional group swap) results from a cascade of SNAr reactions, which are facilitated by azidoazomethine-tetrazole (azide-tetrazole) tautomeric equilibrium. The formation of Meisenheimer-type intermediates as tetrazolopurine tautomers was supported by various spectroscopic methods, including 15N NMR. Copyright: CC BY-NC 4.0

Pieteikuma datums
11.06.2020.
Atslēgas vārdi
MedicinePharmacologyEvolutionary BiologyChemical sciencesInformation systemsInfectious diseasesComputational Biology15 n nmrS N Ar reactionsSodium Azideoptimized reaction conditions6- azido -2-sulfonylpurine derivativessulfonyl group dance
DOI
10.1021/acs.joc.9b03518.s002