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Synthesis, NMR and MS study of novel N-sulfonylated purine derivatives

Žinić, Biserka; Krizmanić, Irena; Vikić-Topić, Dražen; Srzić, Dunja; Žinić, Mladen (2001) Synthesis, NMR and MS study of novel N-sulfonylated purine derivatives. Croatica Chemica Acta, 74 (2). pp. 399-414. ISSN 0011-1643

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Tosylation and mesylation of adenine (1) at room temperature give regioselectively N-9-sulfonylated purines 2 and 5. Excess of TsCl or MsCl at higher reaction temperatures leads to formation of unstable N-6,N-9-disulfonylated products 3 and 6, which easily transform into the corresponding N-6-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.

Item Type: Article
Uncontrolled Keywords: synthesis; N-9-sulfonyl; N-6-sulfonyl; N-6,N-9-disulfonyl purine derivatives; NMR study; MS study; adenosine
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
NMR Center
Project titleProject leaderProject codeProject type
Projektiranje i sinteza supramolekularnih sustavaMladen Žinić00980703MZOS
Sastav, svojstva i dinamika plinskih sustavaTomislav Cvitaš00980601MZOS
Depositing User: Biserka Žinić
Date Deposited: 20 Nov 2013 10:05

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