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A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines.

  作者 Ermolat'ev, Denis S.;Van der Eycken, Erik V.;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-17;  页码  6691-6697  
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[摘要]A new divergent and efficient synthesis of substituted 2-aminoimidazoles and has been developed starting from readily available 2-aminopyrimidines and a-bromocarbonyl compds., using conventional heating or microwave irradn. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1-ium salts, e.g., I, with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles, e.g., II, while the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts, e.g., III, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles, e.g., IV. The likely pathway of the transformations was identified by characterization of the intermediates.

 
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