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Paper | Regular issue | Vol 36, No. 6, 1993, pp.1217-1223
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6047
Reactivity of Isoquinoline Alkaloids with Benzyne

Manuel Paz, Carlos Saá, Enrique Guitián, Luis Castedo,* and José Manuel Saá

*Departamento de Química Orgánica, Sección de Alcaloides del C.S.I.C, Facultad de Química, Universidad de Santiago, 15706 Santiago de Compostela, Spain

Abstract

Benzyne reacts with tertiary aporphines, benzylisoquinolines and cularines by successive β and α eliminations, giving rise to N,N-diphenylarylethylamines. Secondary aporphines (noraporphines) yield N-phenylnoraporphines. Whereas dehydroaporphines undergo α elimination, the corresponding nordehydroaporphines suffer both C and N phenylations by way of an ene reaction followed by N-phenylation of the resulting 7-phenyldehydronoraporphine (aporphine numbering).