title: Synthesis and photochemical behavior of the tetrazolo tautomer of 2-azido-4-pyrimidinone-2'-deoxyriboside.
abstract: The 2-azido analogue of 2'-deoxyuridine was prepared in three steps from 2'-deoxy-2-thiouridine. The sulfur atom of the 2-thio nucleoside was methylated and then displaced by hydrazine to furnish the corresponding 2-hydrazino derivative. After diazotization, the 2-azido compound that exists as its tetrazolo tautomer was obtained. Upon UV irradiation in aqueous solution, the title compound led to isocytosine.
authors.affiliation: Institut de Chimie Moléculaire de Reims, Université de Reims Champagne Ardenne, CNRS UMR 6229, UFR de Pharmacie, 51 rue Cognacq-Jay, 51096 Reims cedex, France.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Gourdain
authors.forename: Christian
authors.initials: C
authors.lastname: Petermann
authors.forename: Agathe
authors.initials: A
authors.lastname: Martinez
authors.forename: Dominique
authors.initials: D
authors.lastname: Harakat
authors.forename: Pascale
authors.initials: P
authors.lastname: Clivio
mesh_terms: D001386:Azides / Q000737:chemistry; D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D007536:Isomerism; D055668:Photochemical Processes; D013777:Tetrazoles / Q000737:chemistry*; D014466:Ultraviolet Rays
chemical_list: C558816:2-azido-4-pyrimidinone-2'-deoxyriboside; D001386:Azides; D013777:Tetrazoles; C045574:1H-tetrazole; D003855:Deoxyribose