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Isocyanide-Based Three-Component Synthesis of Highly Substituted 1,6-Dihydro-6,6-dimethylpyrazine-2,3-dicarbonitrile, 3,4-Dihydrobenzo[g]quinoxalin-2-amine, and 3,4-Dihydro-3,3-dimethyl-quinoxalin-2-amine Derivatives

  作者 Shaabani, A; Hajishaabanha, F; Mofakham, H; Mahyari, M; Lali, B  
  选自 期刊  Helvetica Chimica Acta;  卷期  2012年95-2;  页码  246-254  
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[摘要]A novel and efficient isocyanide-based multicomponent reaction between alkyl or aryl isocyanides 1, 2,3-diaminomaleonitrile (2), naphthalene-2,3-diamines (6) or benzene-1,2-diamine (9), and 3-oxopentanedioic acid (3) or Meldrum's acid (4) or ketones 7 was developed for the ecologic synthesis, at room temperature under mild conditions, of 1,6-dihydropyrazine-2,3-dicarbonitriles 5a5f in H2O without using any catalyst, and of 3,4-dihydrobenzo[g]quinoxalin-2-amine and 3,4-dihydro-3,3-dimethyl-quinoxalin-2-amine derivatives 8a8g and 10a10e, respectively, in the presence of a catalytic amount of p-toluenesulfonic acid (TsOH) in EtOH, in good to excellent yields (Scheme 1).

 
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