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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 7, pp 850–855 | Cite as

Cycloaddition of 2-acylmethyl-1H-benzimidazoles to 4-arylidene-1,3-oxazol-5-ones

  • I. B. Dzvinchuk
  • M. O. Lozinskii
Article

Abstract

Cycloaddition of 2-phenacyl-1H-benzimidazole to 2-phenyl-or 2-methyl-4-arylidene-1,3-oxazol-5-ones occurs regioselectively to form the previously unknown N-(3-aryl-4-benzoyl-1-oxo-1,2,3,4-tetrahydropyrido[1,2-a]benzimidazol-2-yl)benz-and-acetamides. The analogous cycloaddition of the 2-acetonyl-1H-benzimidazole is complicated by prototropic isomerization and leads to the corresponding 1,2,3,5-tetrahydropyrido[1,2-a]benzimidazole.

Keywords

azlactones benzimidazoles pyrido[1,2-a]benzimidazoles [3+3]cycloaddition isomerization regioselectivity 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • I. B. Dzvinchuk
    • 1
  • M. O. Lozinskii
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKiev

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