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Communication | Regular issue | Vol 4, No. 8, 1976, pp.1371-1376
Published online, 1st January, 1970
DOI: 10.3987/R-1976-08-1371
Photocyclization of N-Chloroacetyl-2-methoxy- and 2,4-dimethoxyphenethylamines to 4-Azabicyclo[5.3.1]undeca-9-ene-3,8-diones

Yohmei Okuno and Osamu Yonemitsu*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


When N-chloroacetyl-2,4-dimethoxyphenethylamine (3) was irradiated, photocyclization occurred to form a transient cation intermediate (1), which was immediately attacked by a hydroxide ion to yield 11-hydroxy-10-methoxy-4-azabicyclo[5.3.1]undeca-9-ene-3,8-dione (5). Similarly, on irradiation, N-chloroacetyl-2-methoxyphenethylamine (8) gave the same type compound, 11-hydroxy-4-azabicyclo[5.3.1]undeca-9-ene-3,8-dione (9). Mechanistic consideration was also presented.