5-bromo- and 5-iodo-N-1-sulfonylated cytosine derivatives. Exclusive formation of keto-imino tautomers

Žinić, Biserka; Krizmanić, Irena; Vikić-Topić, Dražen; Žinić, Mladen (1999) 5-bromo- and 5-iodo-N-1-sulfonylated cytosine derivatives. Exclusive formation of keto-imino tautomers. Croatica Chemica Acta, 72 (4). pp. 957-966. ISSN 0011-1643

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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-d(6) solution, while N-1-sulfonylated cytosine 5 appears as a common keto-amino tautomer.

Item Type:	Article
Uncontrolled Keywords:	synthesis; N-1-sulfonylated cytosine derivatives; 5-bromo and 5-iodocytosine derivatives; NMR study; keto-imino and keto-amino tautomers; oligonucleotides; analogs
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry NMR Center
Projects:	Project title Project leader Project code Project type Projektiranje i sinteza supramolekularnih sustava Mladen Žinić 00980703 MZOS
Depositing User:	Biserka Žinić
Date Deposited:	25 Nov 2013 12:06
URI:	http://fulir.irb.hr/id/eprint/1114

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