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FACILE SYNTHESIS OF 3-(SUCCINIMID-3-YL)-2-OXO-2,3-DIHYDROIMIDAZO[1,2-a]PYRIDINE DERIVATIVES BY SEQUENTIAL INTRA- AND INTERMOLECULAR MICHAEL REACTIONS BETWEEN 2-AMINOPYRIDINES AND MALEIMIDES

  作者 SHIMO TETSURO; ITOH TOMOKO; ARAKI YASUTAKA; IWANAGA TETSUO; SHINMYOZU TERUO; SOMEKAWA KENICHI  
  选自 期刊  Heterocycles;  卷期  2011年83-1;  页码  47-55  
  关联知识点  
 

[摘要]3-(Succinimid-3-yl)-2-oxo-2,3-dihydroimidazo[1,2-a]pyridine derivatives (3 and 4) were prepared through a one-pot reaction from 2-aminopyridines (1) by acylation with maleimides (2) and followed by an intramolecular Michael addition, and a subsequent second Michael addition with another molecule of 2. The diastereomeric configurations of the products were confirmed by X-ray crystal analyses. The reaction mechanism of the accumulated three types of additions between 1 and two equimolar amounts of 2 was calculated using MOPAC-PM6 molecular simulations and the competing addition reactions as hard and soft reactions were explained by HSAB theory.

 
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