Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction
Yulei Zhao1, Yang Yuan1, Xiaoyu Wang1
1Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 500 Dongchuan Road, Shanghai 200241, China.
Abstract:
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 (Cs2CO3) was indispensable for the hydrogen migration.
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