Pd-catalyzed sequential intramolecular annulation/intermolecular 3+2 cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles: synthesis of spiroheterocycles

• Published in: Chemical communications (Cambridge, England) Vol. 60; no. 76; p. 10516
• Main Authors: Dong, Yujie, Liu, Jun, Ning, Rongjin, Yang, Fazhou, Zhang, Cheng, Guo, Hongchao
• Format: Journal Article
• Language: English
• Published: 20.09.2024
• ISSN: 1364-548X; 1364-548X
• DOI: 10.1039/d4cc03551h

Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various 5-allenyloxazolidine-2,4-diones reacted with 1,3-dipoles such as nitrile N-oxides, azomethine imines or nitrilimines to give a series of functionalized spiroheterocycles in high yields. The scale-up reaction and further derivation of products were successful. A plausible mechanism was also proposed based on the control experiments.Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various 5-allenyloxazolidine-2,4-diones reacted with 1,3-dipoles such as nitrile N-oxides, azomethine imines or nitrilimines to give a series of functionalized spiroheterocycles in high yields. The scale-up reaction and further derivation of products were successful. A plausible mechanism was also proposed based on the control experiments.