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Communication | Regular issue | Vol 22, No. 9, 1984, pp.1969-1972
Published online, 1st January, 1970
DOI: 10.3987/R-1984-09-1969
Ring Transformation of 1-Azadibenzo[c,f]bicyclo[3.3.1]nona-3,6-dienes: Novel Routes to Dibenzopyrrolizidine and Dibenzotropane

Takashi Nomoto and Hiroaki Takayama*

*Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1 Suarashi, Sagamiko-machi, Tsukui-gun, Kanagawa 199-0195, Japan


Base-induced reactions of N-methyl quaternary salts of 11b-methyl-7,11b-dihydro-5H-isoindolo[2,3-b]isoindole (4), which were effectively transformed from readily available 1-azadibenzo[c,f]bicyclo[3.3.1]nona-3,6-dienes (1), were examined and consequently, 5,12-dimethyl-5,10-imino-10,11-dihydro-5H-dibenzo[a,d]cycloheptens (6) and 6,10b-dimethyl-5,6,6a,10b-tetrahydrobenzo[3,4]cyclobut[l,2-c]isoquinolines (7) were obtained via Stevens rearrangement.