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?

RSC Advances Pub Date: 2014-10-30 DOI: 10.1039/C4RA11128A

Abstract

Efficient synthesis of a library of novel benzopyrido[1,4]oxazepinones was accomplished by Cs2CO3-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.

Graphical abstract: 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
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