101321-87-3Relevant academic research and scientific papers
PREPARATION OF SOME DERIVATIVES OF BENZOQUINOLIZINE
Silhankova, Alexandra,Trska, Petr,Vlkova, Daniela,Ferles, Miloslav
, p. 1048 - 1056 (2007/10/02)
Reaction of 1,2,3,4-tetrahydroquinoline with 1-chloro-2,3-epoxypropane afforded 1-(3-chloro-2-hydroxypropyl)-1,2,3,4-tetrahydroquinoline (IIb) which was thermolabile and on heating in vacuo was converted into 2,3,6,7-tetrahydro-1H,5H-benzoquinolizin-2-ol (Ib).This compound reacted with acetic anhydride and p-toluenesulfonyl chloride to give 2-acetoxy-2,3,6,7-tetrahydro-1H,5H-benzoquinolizine (Ic) and 2-(p-toluenesulfonyloxy)-2,3,6,7-tetrahydro-1H,5H-benzoquinolizine (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-benzoquinolizine-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-benzoquinolizine-2,6-diols (If).Dehydration with potassium hydroxide converted the diols Ie into 1H,7H-benzoquinolizine (VIa), the diols If into 9-methoxy-1H,7H-benzoquinolizine (VIb).Treatment of Ib with phosphorus pentoxide led to 2,3,6,7-tetrahydro-1H,5H-benzoquinolizine (julolidine, Ia).
