INFIQC 05475
INSTITUTO DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Unidad Ejecutora - UE
artículos
Título:
A Novel Approach to the Synthesis of 6-Substituted Uracils in Three-Step, One-Pot Reactions
Autor/es:
JAVIER I. BARDAGÍ; ROBERTO A. ROSSI
Revista:
JOURNAL OF ORGANIC CHEMISTRY
Editorial:
American Chemical Society
Referencias:
Año: 2008 vol. 73 p. 4491 - 4495
ISSN:
0022-3263
Resumen:
From the commercial 6-chloro-2,4-dimethoxypyrimidine (1) and by a photostimulated reaction with Me3Sn- ions, 2,4-dimethoxy-6-(trimethylstannyl)pyrimidine (2) was obtained in 95% yield. By the crosscoupling reaction of 2 with 1-iodonaphthalene as electrophile catalyzed by Pd (Stille reaction), 2,4- dimethoxy-6-(naphthalen-1-yl)pyrimidine (9) was obtained in 76% yield. By hydrolysis of 9, 6-(1- naphthyl)uracil was obtained in 98% of isolated yield. When the three steps (SRN1 reaction-cross coupling reaction-hydrolysis) were performed in a one-pot reaction, 6-substituted uracils (1-naphthyl, 4-chlorophenyl, 3-chlorophenyl, 2,3,4,5,6-pentafluorophenyl) were obtained (43-57%) of isolated pure products. When the electrophile was a benzoyl chloride, 6-benzoyl uracil (54%) and 6-(2-chlorobenzoyl) uracil (49%) were obtained in isolated pure products.
