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Site‐Selective Convergent Synthesis of Spiroacridines through a Cascade Reaction of Enaminones with Acenaphthoquinone: An Efficient Construction of Multiple C−C and C–Heteroatom Bonds
Author(s) -
Chen XueBing,
Wang XueQuan,
Hong Yong,
Liu Wei
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600148
Subject(s) - chemistry , stereocenter , regioselectivity , ring (chemistry) , cascade reaction , heteroatom , combinatorial chemistry , aryl , cascade , stereochemistry , catalysis , enantioselective synthesis , organic chemistry , alkyl , chromatography
A highly efficient strategy has been developed for the regioselective synthesis of 9‐spiroacridine derivatives that have potential biochemical interest. The one‐pot cascade reaction of enaminones and acenaphthoquinone in the presence of para ‐toluenesulfonic acid involved at least five reactive sites and generated two σ bonds, two types of C−N bonds, one stereocenter, and a dihydropyridine ring. The established protocol explores the chemistry of enaminones by employing its three reactive sites (i.e., N ‐aryl nitrogen, β‐carbon, and C=O carbon atoms).