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One‐Pot Synthesis of Phenanthridinones by Using a Base‐Catalyzed/Promoted Bicyclization of α,β‐Unsaturated Carbonyl Compounds with Dimethyl Glutaconate
Author(s) -
Li Lei,
Chen JiaJia,
Kan XingLan,
Zhang Lu,
Zhao YuLong,
Liu Qun
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500414
Subject(s) - chemistry , annulation , aromatization , intramolecular force , domino , intermolecular force , base (topology) , combinatorial chemistry , catalysis , organic chemistry , molecule , mathematical analysis , mathematics
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.