Collect. Czech. Chem. Commun. 1985, 50, 1048-1056

Preparation of some derivatives of benzo[ij]quinolizine

Alexandra Šilhánková, Petr Trška, Daniela Vlková and Miloslav Ferles

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Reaction of 1,2,3,4-tetrahydroquinoline with 1-chloro-2,3-epoxypropane afforded l-(3-chloro-2-hydroxypropyl)-l,2,3,4-tetrahydroquinoline (IIb) which was thermolabile and on heating in vacuo was converted into 2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-2-ol (Ib). This compound reacted with acetic anhydride and p-toluenesulfonyl chloride to give 2-acetoxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine (Ic) and 2-(p-toluenesulfonyloxy)-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine (Id), respectively. N,N-Bis(3-chloro-2-hydroxypropyl)aniline (IIIb) on heating gave a mixture of cis- and trans-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-2,6-diols (Ie). The corresponding 4-methoxyaniline derivative afforded analogously a mixture of cis- and trans-9-methoxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-2,6-diols (If). Dehydration with potassium hydroxide converted the diols Ie into 1H,7H-benzo[ij]quinolizine (VIa), the diols If into 9-methoxy-1H,7H-benzo[ij]quinolizine (VIb). Treatment of Ib with phosphorus pentoxide led to 2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine (julolidine, Ia).