Although many derivatives of phenanthridine have been prepared by the Bischler-Napieralski reaction (1), there is no record of attempts to prepare dihydrophenanthridines by application of the related Pictet-Spengler reaction (2). The experiments herein reported were expected to yield 5,6-dihydrophenanthridines as products of the condensation of 2-aminobiphenyls with aldehydes, but all such attempts were unsuccessful.Cyclization of 2-aminobiphenyl with formaldehyde in the presence of hydrochloric acid or sodium carbonate apparently failed since only a resin was isolated. TABLE I Schiff Bases of 2-Amino-3',4,4',5-tetramethoxybinphenyl

Japanese interest in the alkaloid cepharanthine as an antitubercular agent led to the synthesis and evaluation of numerous analogs (1). Most of the synthetic work was done by Tomita and the most active compound which he prepared was 2.7bis(piperidylacetyl)dibenzo-p-dioxin (I). A less active compound was 2,8bis(piperidylaeetyl)dibenzofuran (II) (2).Since cepharanthine has its two nitrogen atoms in tetrahydroisoquinoline rings, it was decided to prepare a dibenzofuran derivative having two tetrahydroisoquinoline rings. A compound similar to the type desired was achieved

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