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Paper | Regular issue | Vol 63, No. 11, 2004, pp.2523-2536
Published online, 17th September, 2004
DOI: 10.3987/COM-04-10176
■ Synthesis of the Novel Bicyclic Oxepinopyrimidine and Fluorinated Pyrrolidinopyrimidines

Sanja Batinac, Draginja Mrvos Sermek, Mario Cetina, Kresimir Pavelic, Mladen Mintas, and Silvana Raic-Malic*

*Department of Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulicev trg 20, 10000 Zagreb, Croatia

Abstract

The new 5,6-disubstituted pyrimidine nucleoside analogues (5-8) were synthesized by addition of the C-6 lithiated pyrimidine derivative to oxirane as key reaction step. The bicyclic tetrahydrooxepinopyrimidine (9) and fluorinated pyrrolidinopyrimidines (12 and 15) were obtained by intramolecular linkage of acyclic chain to the CH2-5 and N-1 of the pyrimidine ring. The structure of compound (9) containing pyrimidine and tetrahydrooxepine skeleton was determined unequivocally by its X-Ray crystal structure analysis.