Azabenzo[c]quinolizine類の合成研究 (第1報)

2,3,4,4a,5,6-Hexahydro-1H-pyrimido[3,4-a]quinolineの合成

抄録

2-(2-Aminoethyl) quinoline (V), obtained by selective catalytic reduction of 2-quinolineacetonitrile (I) over Raney nickel catalyst under high pressure, was reacted with ethyl chlorocarbonate and gave the corresponding urethan (VIII). 1, 2, 3, 4-Tetra-hydro compound (IX), obtained by the reduction of (VIII) over platinum oxide catalyst, was cyclized by fusion at 200° to 2, 3, 4, 4a, 5, 6-hexahydro-1H-pyrimido[3, 4-a]quinolin-1-one (X), which was reduced by lithium aluminium hydride to 2, 3, 4, 4a, 5, 6-hexahydro-1H-pyrimido[3, 4-a]quinoline (XI). (XI) was readily hydrolyzed by mineral acid to 2-(2-aminoethyl)-1, 2, 3, 4-tetrahydroquinoline (VI) and formaldehyde.