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Communication | Regular issue | Vol 12, No. 10, 1979, pp.1311-1313
Published online, 1st January, 1970
DOI: 10.3987/R-1979-10-1311
Cyclisation of γ-Phenylpropyl Isocyanate to 1H-2-Benzazepin-1-one: An Improved Synthesis of Alkaloid Elwesine

Tamaki Fushimi, Hironori Ikuta, Hiroshi Irie,* Kazuyuki Nakadachi, and Shojiro Uyeo

*Faculty of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan


Treatment of γ-(3,4-dimethoxyphenyl)propyl isocyanate with phosphorous oxychloride followed by stannic chloride gave 1H-7,8-dimethoxy-2-benzazepin-1-one in fair yield, providing a convenient method for constructing 1H-benzazepin-1-one derivatives. Application of the procedure on β-[4-acetoxy-1-(3,4-methylenedioxyphenyl)cyclohexyl]propionic acid furnished an improved synthesis of alkaloid elwesine (dihydocrinine) isolated from Amaryllidaceae plant.