Synthesis and Rearrangement of Quinone-Embedded Epoxycyclopentenones: A New Avenue to Pyranonaphthoquinones and Indenopyranones
作者:Saroj R. De、Sujit K. Ghorai、Dipakranjan Mal
DOI:10.1021/jo801961w
日期:2009.2.20
of the Dowd oxidation, are shown to undergo rearrangement to pyranonaphthoquinones (e.g., 28) and their ring contracted homologues (e.g., 29) on flash vacuum pyrolysis at 450 °C and 0.01 Torr. The rearrangement has been demonstrated to be useful for a regiospecific synthesis of lambertellin (3). Similarly, the masked aziridinocyclopentanone 9 rearranges to 2-pyridone (37).
环氧醌(例如24)易于通过简化的Dowd氧化反应从喹诺醇(例如27)一步组装而成,经过重排后生成吡喃并萘醌(例如28)和它们的环收缩同系物(例如29)在450℃和0.01Torr下进行快速真空热解。已经证明该重排对于兰伯特林的区域特异性合成是有用的(3)。类似地,被掩蔽的叠氮基叠氮环戊酮9重新排列为2-吡啶酮(37)。