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Communication | Regular issue | Vol 9, No. 11, 1978, pp.1545-1548
Published online, 1st January, 1970
DOI: 10.3987/R-1978-11-1545
Base-Induced Reactions of N-Methyl Quaternary Salts of 1-Azadibenzo[c,f]bicyclo[3.3.1]nona-3,6-diene and Related Compounds

Hiroaki Takayama,* Takashi Nomoto, Takayoshi Suzuki, Masayuki Takamoto, and Toshihiko Okamoto

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

Abstract

Reactions of N-mthyl quaternary salt (2) of 1-azadibenzo[c,f]bicyclo[3.3.1]nona-3,6-diene (1) with various bases were examined, and consequently, 6-aza-6-methyldibenzo[b,i]bicyclo[3.2.2]nona-2,8-dime (4) was selectively obtained by the reaction of 2 with potassium t-butoxide in dioxane, in contrast 1-aza-1-methyl-5-methylenedibenzo[c,f]octa-3,6-diene (3) was provided as a sole product by the reaction with potassium hydroxide in water, respectively. Isopavine alkaloids, (±)-amurensinine and (±)-reframine were also derived.