1963 年 83 巻 7 号 p. 682-689
Reaction of 2-chloroquinoline with 3-amino propanol gave 2-(3-hydroxypropylamino)-quinoline (I). I was treated with phosphoryl chloride to give the corresponding 4-aza-benzo[c]quinolizine derivative (III). III was reduced to 2, 3, 4, 4a, 5, 6-hexahydro-1H-pyrimido[1, 2-a]quinoline (IVa) over platinium oxide catalyst.
The hydrochloride of IVa absorbed one mole of hydrogen over platinium oxide catalyst to give 1-(3-aminopropyl)-1, 2, 3, 4-tetrahydroquinoline (IVb), whose structure was elucidated by another method of its synthesis. The compound IVa was prepared also by another method, according to the following process. 2-Aminoquinoline was reacted with ethyl 3-chloropropionate to give 1, 2-dihydro-3H-pyrimido[1, 2-a]quinolin-3-one (VII), followed by its catalytic reduction over platinium oxide catalyst to give 1, 2, 4, 4a, 5, 6-hexahydro-3H-pyrimido[1, 2-a]quinolin-3-one (XIII), which was reduced with lithium aluminum hydride to IVa.