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- Title
One-Pot Synthesis of Phenanthridinones by Using a Base-Catalyzed/Promoted Bicyclization of α,β-Unsaturated Carbonyl Compounds with Dimethyl Glutaconate.
- Authors
Li, Lei; Chen, Jia‐Jia; Kan, Xing‐Lan; Zhang, Lu; Zhao, Yu‐Long; Liu, Qun
- Abstract
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.
- Subjects
HETEROCYCLIC compounds synthesis; ORGANIC synthesis; CARBONYL compounds; AMINOPHENOLS; ANNULATION; RING formation (Chemistry); AROMATIZATION
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 22, p4892
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500414