title: Synthesis of 6-alkyluridines from 6-cyanouridine via zinc(II) chloride-catalyzed nucleophilic substitution with alkyl Grignard reagents.
abstract: 6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc(II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6-cyano-2'-deoxyuridine without the protection at the N(3)-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Yu-Chiao
authors.initials: YC
authors.lastname: Shih
authors.forename: Ya-Ying
authors.initials: YY
authors.lastname: Yang
authors.forename: Chun-Chi
authors.initials: CC
authors.lastname: Lin
authors.forename: Tun-Cheng
authors.initials: TC
authors.lastname: Chien
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002384:Catalysis; D003857:Deoxyuridine / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: D000473:Alkanes; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D015032:Zinc; D003857:Deoxyuridine; D014529:Uridine