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Communication | Regular issue | Vol 4, No. 10, 1976, pp.1669-1673
Published online, 1st January, 1970
DOI: 10.3987/R-1976-10-1669
Heterocycles. II. Photochemistry of 4-(3’,4’-Dimethyoxyphenylacetyl)-2-methylisocarbostyril and Its Enol Acetates

Masayuki Onda,* Yoshihiro Harigaya, and Tsutomu Suzuki

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

Abstract

Photolyses of the isocarbostyril (2) and its enol acetates (4) and (5) are examined. The former affords the C-nor-benzo[c]phenanthridine (3). The Z-isomer (4) of the enol acetate isomerizes to, the E-isomer (5) along with formation of the acetylene (6). Photolysis of the E-isomer (5) in the presence of iodine gives the 11-acetoxybenzo[c]phenanthridines (7) and (8). Structures for all photo-products are confirmed on the basis of their NMR spectra.