Original scientific paper

Synthesis, NMR and MS Study of Novel N-Sulfonylated Purine Derivatives

Biserka Žinić ; Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Irena Krizmanić ; HERBOS Chem. Industry, Obrtnička 17, 44000 Sisak, Croatia
Dražen Vikić-Topić ; Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Dunja Srzić ; Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Mladen Žinić ; Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia

Abstract

Tosylation and mesylation of adenine (1) at room temperature give regioselectively N9-sulfonylated purines 2 and 5. Excess of TsCl or MsCl at higher reaction temperatures leads to formation of unstable N6,N9-disulfonylated products 3 and 6, which easily transform into the corresponding N9-monosulfonylated product 4. Two N-sulfonylated purine nucleoside derivatives 12 and 15 have also been prepared. 1D/2D NMR determined the site of sulfonylation and the spatial arrangement of the substituents. MS spectra showed unexpected rearrangement of protonated molecular ions that occurs upon the loss of SO2.

Keywords

synthesis; N⁹-sulfonyl; N⁶-sulfonyl; N⁶; N⁹-disulfonyl purine derivatives; NMR Study; MS Study

Hrčak ID:

131830

URI

https://hrcak.srce.hr/131830

Publication date:

2.4.2001.

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