Tetrahedron p. 905 - 912 (1983)
Update date:2022-08-03
Topics:
Hillard, Russel L.
Parnell, Carol A.
Vollhardt, K. Peter C.
η5-Cyclopentadienyl dicarbonyl cobalt catalyzes the cocyclization of 1,2-bis(propargyl)-1,2,3,4-tetrahydroisoquinolines 4b and 5 with alkynes to provide a novel synthetic entry into the tetrahydroprotoberberine nucleus.By judicious choice of trimethylsilyl substituents, regiocontrol in the D-ring can be achieved.Reaction of 4b with benzonitrile in the presence of the catalyst furnishes the rare isoquino<2,1-b>-2,6-naphthyridine framework, also regioselectively.
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