Premium
Synthesis of Aminonaphthopyranones and Aminonaphthochromenones by Blaise‐Reaction‐Initiated Cascade Procedures
Author(s) -
He Yan,
Zhang Xinying,
Fan Xuesen
Publication year - 2014
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.201402173
Subject(s) - chemistry , reagent , tandem , cascade reaction , combinatorial chemistry , reactivity (psychology) , stereochemistry , cascade , organic chemistry , catalysis , chromatography , medicine , materials science , alternative medicine , pathology , composite material
An efficient one‐pot synthesis of aminonaphthopyranones through the tandem reaction of 2‐(4‐hydroxybut‐1‐ynyl)benzonitriles with Reformatsky reagents has been developed. Using a similar strategy, aminonaphthochromenones were obtained smoothly starting from 2‐[(2‐hydroxyphenyl)ethynyl]benzonitriles. Furthermore, by taking advantage of the versatile reactivity of the amino group, structural manipulations of aminonaphthopyranone were readily undertaken to give naphthopyranone, 10‐hydroxynaphthopyranone and a functionalized 1,1′‐binaphthyl of potential interest for synthetic and medicinal chemistry studies.