Original scientific paper

5-Bromo- and 5–Iodo-N-1-sulfonylated Cytosine Derivatives. Exclusive Formation of Keto-Imino Tautomers

Biserka Žinić ; Ruđer Bošković Institute, P.O.B.1016, HR–10001 Zagreb, Croatia
Irena Krizmanić ; HERBOS Chem. Industry, Obrtnička 17, 44000 Sisak, Croatia
Dražen Vikić-Topić ; Ruđer Bošković Institute, P.O.B.1016, HR–10001 Zagreb, Croatia
Mladen Žinić ; Ruđer Bošković Institute, P.O.B.1016, HR–10001 Zagreb, Croatia

Abstract

N-1-Sulfonylated cytosine 5 and 5-halogeno-N-1-sulfonylated cytosine derivatives 1 and 2 were synthesized by condensation of silylated cytosine or 5-halogenocytosine bases with tosylchloride in acetonitrile, or by the reaction of cytosine or 5-halogenocytosine bases with tosylchloride in pyridine. The NMR evidences are presented, showing that 1 and 2 form exclusively rare keto-imino tautomers in DMSO-d6 solution, while N-1-sulfonylated cytosine 5 appears as a common keto-amino tautomer.

Keywords

synthesis; N-1-sulfonylated cytosine derivatives; 5-bromo and 5-iodocytosine derivatives; NMR study; keto-imino and keto-amino tautomers

Hrčak ID:

132314

URI

https://hrcak.srce.hr/132314

Publication date:

1.12.1999.

Visits: 1.041 *