多环苯并[b]吲哚[3,2,1-de]吖啶的通过顺序烯丙基化、Diels-Alder 环化和氢迁移反应合成。
Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction.
机构信息
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 500 Dongchuan Road, Shanghai 200241, China.
出版信息
J Org Chem. 2017 Oct 20;82(20):11198-11205. doi: 10.1021/acs.joc.7b01614. Epub 2017 Oct 9.
A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels-Alder cyclization and hydrogen migration processes proceeded successively to furnish the polycyclic target molecules. Control reactions suggested the base (CsCO) was indispensable for the hydrogen migration.
通过炔丙基化合物与有机硼的串联反应，描述了苯并[b]吲哚[3,2,1-de]吖啶的立体选择性合成的新方法，仅得到一种非对映异构体。该顺序过程由 Pd(0)催化的炔丙基碳酸酯烯丙基化引发。然后，Diels-Alder 环化和氢迁移过程相继进行，得到多环目标分子。对照反应表明，氢迁移必不可少的是碱（CsCO）。
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