Nickel-Catalyzed Intramolecular Dual Annulation Reaction of Aryl Nitrile-Containing 1,2,3-Benzotriazin-4(3H)-ones: A Pathway To Synthesize Luotonin A and Related Polycyclic Pyrroloquinazolinones

Herein, we report a nickel-catalyzed intramolecular denitrogenative dual annulation reaction of aryl nitrile-containing 1,2,3-benzotriazine-4(3H)-ones to synthesize polycyclic pyrroloquinazolinones with a tolerance of a wide diversity of substituents. This catalytic reaction is the first denitrogenative transannulation of 1,2,3-benzotriazine-4(3H)-one with nitrile, which can be applied as the critical step to synthesize luotonin A with a high step economy.

Automated summary

Here, we report a new nickel-catalyzed reaction that allows for the intramolecular denitrogenative dual annulation of aryl nitrile-containing 1,2,3-benzotriazine-4(3H)-ones, leading to the synthesis of polycyclic pyrroloquinazolinones. This reaction demonstrates a high tolerance towards a wide variety of substituents and can serve as a critical step in the synthesis of luotonin A, showcasing its high step economy.