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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1770–1776 | Cite as

2-Acylthioacetamides in the Biginelli Reaction

  • M. N. Kurmach
  • A. B. Ryabitskiy
  • V. N. BritsunEmail author
Article

We have demonstrated for the first time a Biginelli reaction of 2-acylthioacetamides with aromatic aldehydes and ureas or thioureas, leading to N-Ar1-4-Ar2-6-R1-1-R2-2-oxo(thioxo)-1,2,3,4-tetrahydro-pyrimidine-5-carbothioamides. The regioselectivity of this process matched the concept of hard/soft Lewis acids and bases. It was established that nitrous acid or other oxidants converted the synthesized compounds into N-Ar1-4-Ar2-6-R1-1-R2-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxamides, and not the expected 4-Ar2-6-R1-1-R2-5-(1,3-benzothiazol-2-yl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).

Keywords

2-acylthioacetamides aromatic aldehydes 2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carbothioamides thioureas ureas three-component heterocyclization 

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • M. N. Kurmach
    • 1
  • A. B. Ryabitskiy
    • 1
  • V. N. Britsun
    • 1
    Email author
  1. 1.Institute of Organic Chemistry, National Academy of Sciences of UkraineKyivUkraine

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