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本文报道几个D环为吡唑酮替代的3-去氧-去氢雌马甾酚酮的杂环类似物的合成。2-甲氧羰基-1,2,3,4-四氢菲酮-1(Ⅱ)和2-甲基2-甲氧羰基-1,2,3,4-四氢菲酮-1(Ⅲ)与水合肼反应分别得到1,2,3,4-四氢菲并[1,2-C]二氢吡唑酮-5′(Ⅳ)和1,2,3,4-四氢菲并[1,2-C]4′-甲基-二氢吡唑酮-5′(Ⅴ)。Ⅱ与苯肼缩合得到一个苯基吡唑酮的衍生物(Ⅵ),Ⅵ在乙醇中重结晶或在空气中放置时,转化为一个高熔点物质,证明是双吡唑酮(Ⅶ)。Ⅵ在硫酸二甲酯作用下甲基化得到两个物质,其中一个(熔点135～138℃)与Ⅵ和碘甲烷在封管中反应得到的化合物(Ⅷ)一致,即证明是Ⅵ的N-甲基衍生物;另一个(熔点173～173.5℃)则是O-甲基衍生物(Ⅸ)。
Here we report the synthesis of several heterocyclic ring D rings of pyrazolone substituted 3-deoxy-dehydrostanostatols. 2-methoxycarbonyl-1,2,3,4-tetrahydropinone-1 (II) and 2-methyl 2-methoxycarbonyl-1,2,3,4-tetrahydro-phenanthridin-1 ) With hydrazine hydrate to give 1,2,3,4-tetrahydrophenanthro [1,2-c] -hydropyrazolone-5 ’(IV) and 1,2,3,4-tetrahydrophenanthrene [1,2-C] 4’-methyl-dihydropyrazolone-5 ’(V). Condensation of phenylhydrazine with phenylhydrazine gives a derivative of phenylpyrazolone (VI). When VI is recrystallized in ethanol or left in air, it is converted to a high melting point substance and proved to be bispyrazolone (VII). Methylation of Ⅵ by dimethyl sulfate gives two compounds, one of which (melting point 135-138 ° C) is consistent with the compound (VIII) obtained by the reaction of VI and methyl iodide in the capping tube, that is, N- Methyl derivative; the other (melting point 173-173.5 ° C) is the O-methyl derivative (IX).