Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels–Alder Cyclization, and Hydrogen Migration Reaction

Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels–Alder Cyclization, and Hydrogen Migration Reaction
Yang Yuan, Yanzhong Li, Yulei Zhao, Xiaoyu Wang
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01614

DOI: 10.1021/acs.joc.7b01614

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