Ligand-free copper-catalyzed efficient one-pot access of benzo[b]pyrido[3,2-f][1,4]oxazepinones through O-heteroarylation-Smiles rearrangement-cyclization cascade

Efficient synthesis of a library of novel benzopyrido[1,4]oxazepinones was accomplished by Cs 2 CO 3 -mediated one-pot coupling of N -substituted- o -chloronicotinamides and o -halogenated phenols using cuprous oxide catalysis in DMF at 120 °C through an O -heteroarylation-Smiles rearrangement-cycli...

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Bibliographic Details
Published inRSC advances Vol. 4; no. 98; pp. 55640 - 55648
Main Authors Ganguly, Nemai C., Mondal, Pallab, Roy, Sushmita, Mitra, Partha
Format Journal Article
LanguageEnglish
Published 2014
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Summary:Efficient synthesis of a library of novel benzopyrido[1,4]oxazepinones was accomplished by Cs 2 CO 3 -mediated one-pot coupling of N -substituted- o -chloronicotinamides and o -halogenated phenols using cuprous oxide catalysis in DMF at 120 °C through an O -heteroarylation-Smiles rearrangement-cyclization cascade (16 examples). The C–N bond construction process is biased in favour of Smiles rearrangement allowing regioselective generation of these tricyclic molecular architectures essentially free from Goldberg- N -arylation products in good to excellent yields.
ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA11128A