Photocyclization of N-Chloroacetyl-3-methoxyphenethylamine and N-Chloroacetyl-3, 5-dimethoxyphenethylamine.

Abstract

On irradiation of N-chloroacetyl derivatives of 3-methoxyphenethylamine (VII) and 3, 5-dimethoxyphenethylamine (XV) in 10% aqueous ethanol, 1, 2, 4, 5-tetrahydro-3H-3-benzazepin-2-ones (VIII, IX, and XVI) were synthesized in good yield, whereas in ethanol novel ten-membered lactams (XIII and XVII) were main products. The photo-reaction of N-chloroacetylphenethylamine (XXI) in the presence or absence of veratrol (XXV) gave the intermolecular reaction product (XXVI) or the radical reaction products (XXII and XXIV), which may support the proposed dualistic mechanism.