Copper‐Assisted/Copper‐Free Synthesis of Functionalized Dibenzo[ b , f ]oxepins and Their Analogs  via  a One‐Pot Tandem Reaction | Zendy

Wang Yuqin | Zendy; Chen Yanhong | Zendy; He Qian | Zendy; Xie Yuyuan | Zendy; Yang Chunhao | Zendy

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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.

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