Facile synthesis of halo-substituted tetrahydroisoquinolines and tetrahydro-2-benzazepines via N-acetyl-1, 2-dihydroisoquinolines

CD Perchonock, I Lantos, JA Finkelstein…

Index: Perchonock; Lantos; Finkelstein; Holden Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1950 - 1953

Full Text: HTML

Citation Number: 35

Abstract

-_ addition to a slurry of AlC13 in 1, 2-dichloroethane at room temperature. At least 4 equiv of A1Cl3 were necessary for optimum results; in practice, we utilized 4.6 equiv of A1C13 Workup shortly thereafter afforded the N-acetyldihydroisoquinolines 3. The yields of monohalo products 3a-d ranged from 35 to 55%, while the dichloro products 3e, f were obtained consistently in 6040% yield. The mildness of the cyclization conditions is ...