title: Synthesis of azanucleosides through regioselective ring-opening of epoxides catalyzed by sulphated zirconia under microwave and solvent-free conditions.
abstract: New azanucleosides were obtained using sulphated zirconia (ZS) as catalyst in the nucleophilic oxirane ring opening reaction of 1-allyl-3-(oxiran-2-ylmethyl) pyrimidine-2,4(1H,3H)-dione and 1-allyl-5-methyl-3-(oxiran-2-ylmethyl)-pyrimidine-2,4(1H,3H)-dione, with (S)-prolinol. The new templates were obtained with good yields following a route which exploits the reactivity of epoxides in the presence of sulphated zirconia as catalyst. The key step was carried out using microwave and solvent-free conditions and proceeds with high selectivity.
authors.affiliation: Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana, Av. San Pablo No. 180, México D.F., C.P. 02200, Mexico.
authors.forename: Celia Xochitl
authors.initials: CX
authors.lastname: Hernández-Reyes
authors.forename: Deyanira
authors.initials: D
authors.lastname: Angeles-Beltrán
authors.forename: Leticia
authors.initials: L
authors.lastname: Lomas-Romero
authors.forename: Eduardo
authors.initials: E
authors.lastname: González-Zamora
authors.forename: Rubén
authors.initials: R
authors.lastname: Gaviño
authors.forename: Jorge
authors.initials: J
authors.lastname: Cárdenas
authors.forename: José Antonio
authors.initials: JA
authors.lastname: Morales-Serna
authors.forename: Guillermo E
authors.initials: GE
authors.lastname: Negrón-Silva
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D009705:Nucleosides; D015040:Zirconium; C028541:zirconium oxide