title: Synthesis of cyclobutane nucleosides 2-preparation of thymine and uracil analogues.
abstract: 1-(2-Oxocyclobutyl-4-benzoyloxymethyl)-2,4(1H,3H)-pyrimidinedione and 1-(2-oxocyclobutyl-4-benzoyloxymethyl)-5-methyl-2,4(1H,3H)-pyrimidinedione can be prepared by reaction of uracil and thymine, respectively, with 3-benzoyloxymethyl-2-bromocyclobutanone. The N-alkylation gave both cis and trans isomers with the trans isomer predominating for uracil whereas the trans isomer was the only product which could be isolated for thymine. Both series were subjected to borohydride reduction followed by transesterification with methoxide giving the corresponding uracil and thymine nucleoside analogues. The uracil derivative 1-(2-oxocyclobutyl-4-benzoyloxymethyl)-2,4(1H,3H)-pyrimidinedione was irradiated in aqueous acetonitrile to generate isonucleoside analogues.
authors.affiliation: a Beni-Suef University , Egypt.
authors.forename: Hanan
authors.initials: H
authors.lastname: Afifi
authors.affiliation: b Suez Canal University , Egypt.
authors.forename: Abdelaziz
authors.initials: A
authors.lastname: Ebead
authors.affiliation: c Department of Chemistry, York University , Toronto , Ontario , Canada.
authors.forename: Joseph
authors.initials: J
authors.lastname: Pignatelli
authors.affiliation: c Department of Chemistry, York University , Toronto , Ontario , Canada.
authors.forename: Edward
authors.initials: E
authors.lastname: Lee-Ruff
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003503:Cyclobutanes / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D055668:Photochemical Processes; D013237:Stereoisomerism; D013941:Thymine / Q000031:analogs & derivatives*; D014498:Uracil / Q000031:analogs & derivatives*
chemical_list: D003503:Cyclobutanes; D009705:Nucleosides; D014498:Uracil; D013941:Thymine
keywords: cyclobutane nucleosides; photochemistry; thymine; uracil