【摘 要】
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The tetrahydrocarbazole architecture is a privileged heterocyclic ring system.It not only widely exists in various naturally occurring alkaloids and pharmacologically active compounds,but also is feat
【机 构】
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College of Chemistry and Chemical Engineering,Yangzhou University,Yangzhou,225002
【出 处】
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中国化学会第十六届全国有机合成化学学术研讨会
论文部分内容阅读
The tetrahydrocarbazole architecture is a privileged heterocyclic ring system.It not only widely exists in various naturally occurring alkaloids and pharmacologically active compounds,but also is featured in a large family of synthetic analogues exhibiting a wide spectrum of important bioactivities.Therefore,many elegant methods for the preparation of various tetrahydrocarbazole derivatives have been developed in the past years.Among the many efficient synthetic methodologies for tetrahydrocarbazoles,the [4+2] reaction of 3-vinylindolines with diverse dienophiles has proven to be the most attractive strategy for the synthesis of many carbazole derivatives.The three-component Levy reaction of indole-2-acetate,aldehyde and dienophiles involved the in situ generation of active 3-methyleneindolines and sequential Diels-Alder reaction for synthesis of versatile tetrahydrocarbazoles.1 By employing 3-methyleneoxindoles,2-arylidene-1,3-indanediones and isatylidene malononitrile as active dienophiles,we found that CuSO4 promoted three-component reaction in toluene at 130 ℃ afforded diverse spiro-indoline-carbazole derivatives in ggood yields with high diastereoselectivity.The relative configuration of the obtained spiro compounds were clearly elucidated by determination of a couple of single crystal structures.
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