Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives
The Journal of Organic Chemistry
2020
Jānis Miķelis Zaķis,
Kristers Ozols,
Irina Novosjolova,
Reinis Vilšķērsts,
Anatolijs Mišņovs,
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.
Atslēgas vārdi
Purine, azide, tetrazole, SNAr
DOI
10.1021/acs.joc.9b03518
Hipersaite
https://pubs.acs.org/doi/10.1021/acs.joc.9b03518
Zaķis, J., Ozols, K., Novosjolova, I., Vilšķērsts, R., Mišņovs, A., Turks, M. Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives. The Journal of Organic Chemistry, 2020, Vol. 28, No. 7, 4753.-4771.lpp. ISSN 0022-3263. e-ISSN 1520-6904. Pieejams: doi:10.1021/acs.joc.9b03518
Publikācijas valoda
English (en)