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Isobutyl Nitrite‐Mediated Synthesis of Quinoxalines through Double C−H Bond Amination of N ‐Aryl Enamines
Author(s) -
Jiao YanXiao,
Wei LinSu,
Zhao ChunYang,
Wei Kai,
Mo DongLiang,
Pan ChengXue,
Su GuiFa
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800928
Subject(s) - chemistry , quinoxaline , amination , oxime , nitrite , aryl , double bond , enamine , combinatorial chemistry , derivative (finance) , organic chemistry , medicinal chemistry , catalysis , nitrate , alkyl , financial economics , economics
An efficient and metal‐free double C−H bond amination of N ‐aryl enamines using isobutyl nitrite (IBN) has been developed. This method enables the preparation of functionalized quinoxalines in good to excellent yields and tolerates a variety of N ‐aryl enamines with diverse functional substituents. Mechanistic studies revealed the presence of a key β ‐imino oxime ester intermediate. A quinoxaline derivative could be prepared from β ‐carbonyl ester in one‐pot sequence on a gram scale. Finally, two important quinoxaline scaffolds were easily prepared in moderate yields over two steps.