[1 + 2 + 3] 环化的正规途径：一锅法合成咔唑类和吲哚咔唑类生物碱。
Formal [1 + 2 + 3] Annulation: Domino Access to Carbazoles and Indolocarbazole Alkaloids.
机构信息
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Institute of Molecular and Nano Science , Shandong Normal University , Jinan 250014 , China.
Department of Chemistry, Jilin Province Key Laboratory of Organic Functional Molecular Design and Synthesis , Northeast Normal University , Changchun 130024 , China.
出版信息
Org Lett. 2018 Sep 7;20(17):5348-5352. doi: 10.1021/acs.orglett.8b02266. Epub 2018 Aug 15.
A new formal [1 + 2 + 3] annulation of o-alkenyl arylisocyanides with α, β-unsaturated ketones under metal-, base-, and acid-free conditions is disclosed. This domino reaction provides a general protocol for the efficient and practical synthesis of a wide range of carbazole derivatives from readily available starting materials in a single operation. Furthermore, this methodology was used as the key step in a protecting-group-free synthesis of indolocarbazole alkaloids arcyriaflavin A and racemosin B.
本文报道了一种在无金属、无碱和无酸条件下，通过邻烯基芳基异氰与α,β-不饱和酮的新型[1 + 2 + 3]环加成反应。该串联反应为从易得的起始原料出发，通过一步反应高效、实用合成广泛的咔唑衍生物提供了一个通用方法。此外，该方法还被用于阿克里亚黄素 A 和 racemosin B 这两种吲哚咔唑生物碱的无保护基合成中的关键步骤。
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