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

被引：19

作者：

Ganguly, Nemai C. ^{[1
]}

Mondal, Pallab ^{[1
]}

Roy, Sushmita ^{[1
]}

Mitra, Partha ^{[2
]}

机构：

[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

[2] Indian Assoc Cultivat Sci, Dept Inorgan Chem, Kolkata 700032, India

来源：

RSC ADVANCES | 2014年 / 4卷 / 98期

关键词：

5-HT1A RECEPTOR AGONISTS; DOMINO APPROACH; ULLMANN; DERIVATIVES; ARYLATION;

D O I：

10.1039/c4ra11128a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 degrees 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.

引用

页码：55640 / 55648

页数：9

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