INVESTIGADORES
BAROLO Silvia Maricel
artículos
Título:
Syntheses of Aporphine and Homoaporphine Alkaloids by Intramolecular ortho-Arylation of Phenols with Aryl Halides via SRN1 Reactions in Liquid Ammonia
Autor/es:
SILVIA M. BAROLO; XIN TENG; GREGORY D. CUNY*; ROBERTO A. ROSSI*
Revista:
JOURNAL OF ORGANIC CHEMISTRY
Referencias:
Año: 2006 vol. 71 p. 8493 - 8499
ISSN:
0022-3263
Resumen:
The photostimulated intramolecular ortho-arylation reactions of bromoarenes linked with pendant phenoxy containing N-substituted tetrahydroisoquinolines in liquid ammonia afforded aporphine (54-82% yield) alkaloid derivatives via SRN1 reactions. This strategy was extended for the first time to the synthesis of a homoaporphine derivative (40% yield). Tetrahydroisoquinoline precursors that contained electronwithdrawing groups on nitrogen (i.e., amides, sulfonamides, and carbamates) gave cyclized products, whereas precursors with basic nitrogens (i.e., NH or NMe) either failed to yield cyclized products or gave aporphines in only low yield.
