Nickel-Catalyzed Intramolecular Dual Annulation Reaction of Aryl Nitrile-Containing 1,2,3-Benzotriazin-4(3<i>H</i>)-ones: A Pathway To Synthesize Luotonin A and Related Polycyclic Pyrroloquinazolinones
Vijaykumar H. Thorat, Jen‐Chieh Hsieh
Abstract
Herein, we report a nickel-catalyzed intramolecular denitrogenative dual annulation reaction of aryl nitrile-containing 1,2,3-benzotriazine-4(3 H )-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(3 H )-one with nitrile, which can be applied as the critical step to synthesize luotonin A with a high step economy.
Topics & Concepts
AnnulationChemistryNitrileIntramolecular forceCatalysisArylCombinatorial chemistryNickelMedicinal chemistryOrganic chemistryAlkylQuinazolinone synthesis and applicationsSynthesis and Reactivity of HeterocyclesSynthesis and bioactivity of alkaloids