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Communication | Special issue | Vol 8, No. 1, 1977, pp.89-95
Published online, 1st January, 1970
DOI: 10.3987/S(S)-1977-01-0089
Heterocycles. V. Key Intermediates for Corynoline Analogues

Masayuki Onda,* Yoshihiro Harigaya, and Junya Horie

*School of Pharmaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan

Abstract

The 2-aryl-2-methyl-1-tetralone (2), which is derived from the 2-aryl-1-tetralone (1), affords the cis (5) and trans tetrahydrobenzo[c]phenanthridine (6) by the Leuckart and Bischler-Napieralski reactions. The methiodide (7) of 5 is converted into the cis lactam (10) via oxidation of the pseudo cyanide (9). On bromination and successive dehydrobromination 2 gives the enone (13) which affords the cis (16) and trans dihydrobenzo[c]phenanthridine (17) by the same procedures as above. The methiodide (18) of 16 is reduced to give the cis tetrahydrobenzo[c]phenanthridine (19). The compounds (10) and (19) can be connected with the synthetic methods of corynoline analogues, which were already known.