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Copper‐Assisted/Copper‐Free Synthesis of Functionalized Dibenzo[ b , f ]oxepins and Their Analogs via a One‐Pot Tandem Reaction
Author(s) -
Wang Yuqin,
Chen Yanhong,
He Qian,
Xie Yuyuan,
Yang Chunhao
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200116
Subject(s) - chemistry , acetonitriles , copper , cascade reaction , yield (engineering) , reaction conditions , combinatorial chemistry , tandem , base (topology) , cascade , medicinal chemistry , organic chemistry , catalysis , metallurgy , mathematical analysis , materials science , mathematics , chromatography , acetonitrile , composite material
A simple, convenient, and efficient method for the formation of functionalized dibenzo[ b , f ]oxepins and their analogs bearing both electron‐donating and electron‐withdrawing groups has been developed via a one‐pot cascade reaction. Most starting materials are commercially available 2‐(2‐hydroxyphenyl)acetonitriles and 2‐haloarylaldehydes. The procedure makes use of Cs 2 CO 3 as the base, and DMF as solvent under copper‐assisted/copper‐free conditions. The reaction has a comprehensive group tolerance for substrates. Most of the reactions were complete within 1 h in good‐to‐excellent yields, and the reaction temperatures were relatively low. The protocol could be scaled up to grams without lowering the yield. A reaction mechanism was also proposed.