Unsymmetrical ketones were prepared by successive alkylation of acetone dimethylhydrazone. Application of this reaction to the synthesis of dihydrojasmone is described.
The alkylation of 3-methyl-2-cyclopenten-1-one N, N-dimethylhydrazone was investigated and was found to mone and cis-jasmone were prepared in good yield. Isophorone dimethylhydrazone was also alkylated at the a-position, but for ionone dimethylhydrazone, the reaction occured at the a'-position (methyl carbon), not the a-position of the hydrazone.
Aus den Tetralonen (I) erhält man mit Formaldehyd (II) und den sekundären Aminen (III) die Aminoketone (IV), die nach Reduktion zu den Alkoholen (V) mit Salzsäure in die Allylamine (VI) übergeführt werden.
Das nach Literaturverfahren erhaltene Acetonhydrazon (II) wird mit den Alkylhalogeniden (III) zu den Monoalkylderivaten (IV) umgesetzt, die in einem weiteren Alkylierungsschritt mit den Alkylhalogeniden (V), die zum Teil mit den Alkylhalogeniden (III) identisch sind, zu den asymm. Dialkylhydrazonen (VI) umgesetzt werden, aus denen dann die asymm. Ketone (VII) erhalten werden.
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