Phenolic Cyclization. IX. Syntheses of Benz [<I>c</I>] phenanthridine and Related Compounds

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  • Studies on the Syntheses of Heterocyclic Compounds. CDIX

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Trans-1-Amino-1, 2, 3, 4-tetrahydro-2-(3-methoxyphenyl) naphthalene (IV) was synthesized by the reduction of oxime (VIII). Mannichr eaction of IV with formalin and acetaldehydea ffordedb enz [c] phenanthridines, XI and XII, respectively. The amine (IV) was treated with pyridineh ydrochloridteo givep henolic base (V). Thec ondensation, of V with carbonylc ompoundws asi nvestigatedto givet he corresponding benz [c] phenanthridine derivatives (XV-XX). In the case of benzaldehydec, yclizationw asf ound to occur at both positions, para and ortho to the hydroxylg roup to give XVII, XVIII, and XX. Furthermorea, cetylationo f these phenolic benz [c] phenanthridines and an alternative synthesis of XII were also described.

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