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Modulating the Reactivity of Heterocyclic Ketene Animals in MCR: Selective Construction of Tetrahydrobenzo[b]imidazo[3,2,1-iota j][1,8]naphthyridines

  作者 WEN LIRONG; LIU CHAO; LI MING; WANG LIJUAN  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-22;  页码  7605-7614  
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[摘要]Two new kinds of tetrahydrobenzo[b]imidazo[3,2,1-iota j][1,8]naphthyndine derivatives have been successfully synthesized by cascade reactions including Knoevenagel condensation, aza-ene reaction, imine-enamine tautomenzation, cyclocondensation, and intramolecular SNAr of precursors 2-(2-chloroaroyl)methyleneimidazolidines with aromatic aldehydes and ethyl acetoacetate or Meldrum's acid under mild conditions, respectively These studies highlighted the concept of a substrate-design approach to the development of novel multicomponent reactions by simply incorporating an o-halo group into the aryl ring of 2-benzoyl-methyleneimidazolidine as new synthons In this domino reaction, at least six different active sites are involved, two C-C bonds, two C-N bonds, and two new rings are constructed with all reactants efficiently utilized in the chemical transformation

 
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