An ANTIMALARIAL ALKALOID FROM HYDRANGEA. VII. 3-[Β-Keto-Γ-(5-Hydroxy-2-Piperidyl)propyl]-4-Quinazolone, AN ISOMER

Abstract

The synthesis of an isomer of the Hydrangea alkaloid, 3-[|8-keto-Y-(5-hydroxy-2-piperidyl)propyl]-4-quinazolone, via the key intermediate 3-(2,4-diketo-7* methoxy-8-benzamidooctyl)-4-quinazolone has been described.Claisen condensation with l-phthalimido-2-hydroxy-5-hexanone has been unexpectedly found to take place on the methylene group rather than the methyl group.Pearl River, N.Y.

An ANTIMALARIAL ALKALOID FROM HYDRANGEA. VIII. ATTEMPTED SYNTHESIS OF 3-[Β-Keto-Γ-(4-Hydroxy-2-Piperidyl)propyl]-4-Quinazolone BY THE DIKETONE APPROACH

“…This approach was also used successfully for the 5-hydroxypiperidyl isomer of II (2). The synthesis of the appropriate diketone, I, and the unsuccessful attempts to convert I to II are now described.…”