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Communication | Regular issue | Vol 60, No. 8, 2003, pp.1779-1786
Published online, 24th June, 2003
DOI: 10.3987/COM-03-9801
A New Route to Papaverine Analogs via Photocyclization of Substituted N-Acyl-α-dehydrophenylalaninamides

Hideki Hoshina, Kei Maekawa, Keisuke Taie, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

(Z)-N-Phenylacetyl-α-dehydro(3,4-dimethoxyphenyl)alaninamide derivatives [(Z)-1] were prepared in satisfactory yields, starting from 3,4-dimethoxybenzaldehyde. On irradiation in methanol, regioselective photocyclization of these derivatives proceeded to give papaverine analogs in good yields. Substituents introduced into (Z)-1 were found to exert only a minor effect on the conversion of the starting isomers (1) as well as on the selectivity of the analogs which were formed along with 1-azetines.