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Dearomative cyclization of pyridines/isoquinolines with cyclopropenones: access to indolizinones and benzo-fused indolizinones.

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Dearomatization reactions provide a rapid approach to construct complicated molecules that are difficult to synthesize by traditional methods from simple aromatic compounds. Herein, we report an efficient dearomative [3+2] cycloaddition… Click to show full abstract

Dearomatization reactions provide a rapid approach to construct complicated molecules that are difficult to synthesize by traditional methods from simple aromatic compounds. Herein, we report an efficient dearomative [3+2] cycloaddition reaction of 2-alkynyl pyridines with diarylcyclopropenones, leading to the synthesis of densely functionalized indolizinones in moderate to good yields under metal-free conditions. In addition, this strategy can also be employed in dearomative cyclization of isoquinolines to access a variety of benzo-fused indolizinones. Density functional theory (DFT) calculations revealed that an appropriate substituent at the 2-position of pyridine is crucial to the dearomatization process.

Keywords: cyclization pyridines; dearomative cyclization; benzo fused; fused indolizinones; access

Journal Title: Chemical communications
Year Published: 2023

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