A new strategy for the highly efficient construction of functionalized phenanthridinones has been developed by starting from readily available acyclic α,β‐unsaturated carbonyl compounds that have a 2‐aminophenyl group at the β‐position or carbonyl carbon and dimethyl glutaconate. The domino reaction involves an intermolecular [3+3] annulation followed by an intramolecular aza‐cyclization/aromatization process and allows for the synthesis of polysubstituted dihydrophenanthridinone and phenanthridinone derivatives in high to excellent yields under extremely mild conditions (i.e., transition‐metal‐free and open to air) in a single step.
A novel DBU-mediated oxidative cyanation of α-amino carbonyl compounds by using air as the sole oxidant was developed under mild metal-free conditions for the first time. The reaction involves a tandem oxidation/Strecker reaction/oxidation process and provides a new and efficient method for the construction of α-iminonitriles in good to high yields in a single step.
DBU-Mediated Metal-Free Oxidative Cyanation of -Amino Carbonyl Compounds: Using Molecular Oxygen as the Oxidant. -This DBU-mediated oxidative cyanation of -amino carbonyl compounds using air as the sole oxidant involves a tandem oxidation/Strecker reaction/oxidation process and provides an efficient method for the construction of -iminonitriles. -(LI, L.; WANG, Q.; LIU, P.; MENG, H.; KAN, X.-L.; LIU, Q.; ZHAO*, Y.-L.; Org. Biomol. Chem. 14 (2016) 1, 165-171, http://dx.
One-Pot Synthesis of Phenanthridinones by Using a Base-Catalyzed/Promoted Bicyclization of ,-Unsaturated Carbonyl Compounds with Dimethyl Glutaconate. -In the base-promoted reactions of compounds (VI) complete aromatization of the C-ring is observed. -(LI, L.; CHEN, J.-J.; KAN, X.-L.; ZHANG, L.; ZHAO*, Y.-L.; LIU, Q.; Eur. J. Org. Chem. 2015, 22, 4892-4899, http://dx.
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