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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


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).