アミノキノリン誘導体の合成研究(第6報) : Pyrimido[1,2-α]quinoline誘導体の合成

概要

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Reaction of the alkylated derivatives of 2-chloroquinoline with 3-aminopropanol afforded 2-(3-hydroxypropylamino) quinoline derivatives. The hydroxyl group in the ω-position in the side chain was chlorinated with phosphorus pentachloride and phosphoryl chloride and the hydrochlorides (Xa-f) of 2-(3-chloropropylamino) quinoline derivatives were obtained. These hydrochlorides were neutralized with sodium hydrogencarbonate to pH 7.0-7.1 in order to obtain free 2-(3-chloropropylamino) quinoline but the precipitated crystals were not those of the anticipated free compound but was found to be 1,2,3,4-tetrahydropyrimido [1,2-a] quinolinium chloride, a compound formed by the additional cyclization into a six-membered ring between the chlorinated carbon atom and the non-conjugated electron pairs in the sp orbital of the nitrogen atom in the quinoline ring during neutralization. Treatment of this quaternary salt with alkali resulted in the bonding of OH^- with the carbon at 4a position in the ring due to the E effect of positively charged ring nitrogen, and the pseudo base, i.e., methyl dreivative of 4a-hydroxy-1,2,3,4-tetrahydropyrimido [1,2-a] quinoline, was obtained. This compound was found to undergo isomerization to a lactam when heated.
公益社団法人日本薬学会の論文
1969-06-25