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. Issue 7 (11th May 2016)

• Record Type: Journal Article
• Authors: Chen, Xue‐Bing; Wang, Xue‐Quan; Hong, Yong; Liu, Wei
• Is Part Of: Asian journal of organic chemistry. Volume 5:Issue 7(2016)
• Page Start: 907
• Page End: 913
• Publication Date: 2016-05-11
• Subjects: cyclization -- domino reactions -- nitrogen heterocycles -- regioselectivity -- spiro compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201600148
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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). Abstract : Tandem not random : 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 between enaminones and acenaphthoquinone in the presence of para ‐toluenesulfonic acid generated the two carbon–carbon and two carbon–heteroatom bonds of the heterocyclic product, p ‐TSA= para ‐toluenesulfonic acid.