A new synthetic route to the 1,5-methanoazocino[4,3-b]indole is described. The aim of the present study is to provide a tetracyclic skeleton for the synthesis of pentacyclic Strychnos alkaloids (tubifolidine and strychnopivotine). Starting from a carbazole derivative, the ring closure was achieved by an intramolecular aldol reaction. The final product was obtained in 45% in the overall yield over 7 steps.
The acid dissociation constants, pK
a, of eight biologically active imidazole derivatives were determined
using a spectroscopic technique. Using the obtained acid dissociation constants, attempts were made to
elucidate the structures and protonation mechanisms of these derivatives. Four of eight molecules were
found to behave as Hammett base for the first protonation.
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