作者: TATSUO HAMADA , YOHMEI OKUNO , MASAYUKI OHMORI , TAKAO NISHI , OSAMU YONEMITSU
DOI: 10.1248/CPB.29.128
关键词: Aniline 、 Amide 、 Nitrogen 、 Excimer 、 Photochemistry 、 Intramolecular force 、 Benzylamine 、 Quantum yield 、 Alkyl 、 Chemistry
摘要: Although N-chloroacetyl derivatives of benzylamines (2, 8) and anilines (21, 25, 29) disappeared quite rapidly when irradiated with a high pressure mercury lamp, no photocyclization to six- five-membered lactams occurred. Measurements fluorescence quenching disappearance quantum yields N-chloroacetyl-(3, 4-dimethoxylphenyl)-alkylamines having various lengths alkyl chain revealed that the shorter is, more efficient exciplex formation is. Therefore, failure seemed be due trans conformation amide bonds in benzylamine aniline derivatives. Introduction an group on nitrogen changed stable amides from cis, hence N-alkyl-N-chloroacetylbenzylamines (11, 13, 15, 17, 19) readily gave corresponding 1, 2, 3, 4-tetrahydroisoquinolin-3-ones (12, 14, 16, 18, 20) irradiation. Oxindoles (36, 38, 40, 41, 43, 46) were similarly synthesized by N-alkyl-N-chloroacetylanilines (35, 37, 39, 42, 45).