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Communication | Regular issue | Vol 9, No. 10, 1978, pp.1429-1432
Published online, 1st January, 1970
DOI: 10.3987/R-1978-10-1429
Double-Cyclization Reactions of 1-Dibenzylamino-2-propanone and Related Compounds

Hiroaki Takayama,* 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

1-Dibenzylamino-2-propanone and its 1-methyl derivative, 2-benzylamino-1-cyclohexanone, 2-benzylamino-1-cyclopentanone, and N,N-dibenzyl-p-X(X=H,Br,NO2)-phenacylamine, by employing 70%-perchloric acid or triflic acid as cyclization catalyst, afforded 1-aza-5-methydibenzo[c,f]bicyclo[3.3.1]nona-3,6-diene and its 9-methyl derivative, 1-azadibenzo[h,m]tricyclo[5.3.3.02,7]trideca-8,12-diene, 1-azadibenzo[g,l]tricyclo[4.3.3.02,6]dodeca-3,6-diene, and 1-aza-5-p-X(X=H,Br,NO2)-phenyldibenzo[c,f]bicyclo[3.3.1]nona-3,6 diene, in 74-95% isolated yields, respectively.