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Copper‐Catalyzed Domino Synthesis of 2‐Imino‐1 H ‐imidazol‐5(2 H )‐ones and Quinoxalines Involving CC Bond Cleavage with a 1,3‐Dicarbonyl Unit as a Leaving Group
Author(s) -
Yang Yan,
Ni Fan,
Shu WenMing,
Wu AnXin
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403001
Subject(s) - domino , intramolecular force , chemistry , cascade reaction , bond cleavage , dehydrogenation , catalysis , combinatorial chemistry , cleavage (geology) , medicinal chemistry , stereochemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
Although 2‐imino‐1 H ‐imidazol‐5(2 H )‐ones have important biological activities in metabolism, their synthesis has rarely been investigated. Quinoxalines as “privileged scaffolds” in medicinal chemistry have been extensively investigated, but the development of novel and efficient synthetic methods remains very attractive. Herein, we have developed two copper‐catalyzed domino reactions for the synthesis of 2‐imino‐1 H ‐imidazol‐5(2 H )‐ones and quinoxalines involving CC bond‐cleavage with a 1,3‐dicarbonyl unit as a leaving group. The domino sequence for the synthesis of 2‐imino‐1 H ‐imidazol‐5(2 H )‐ones includes aza‐Michael addition, intramolecular cyclization, CC bond‐cleavage, 1,2‐rearrangement, and aerobic dehydrogenation reaction, whereas the domino sequence for the synthesis of quinoxalines includes aza‐Michael addition, intramolecular cyclization, elimination reaction, and CC bond‐cleavage reaction. The two domino reactions have significant advantages including high efficiency, mild reaction conditions, and high tolerance of various functional groups.