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<p>The reaction of lithium (<i>Z</i>)-1,1,1-trifluoro-4-oxo-4-(pyridin-3-yl)- or (<i>Z</i>)-1,1,1-trifluoro-4-oxo-4-(4-pyridin-4-yl)but-2-en-2-olate with ammonium acetate in glacial AcOH afforded new amino enones containing an amino group geminal to the fluoroalkyl substituent, (<i>Z</i>)-3-amino-4,4,4-trifluoro-1-(pyridin-3-yl)- and (<i>Z</i>)-3-amino-4,4,4-trifluoro-1-(pyridin-4-yl)but-2-en-1-one, respectively. On heating in AcOH under reflux, (<i>Z</i>)-3-amino-4,4,4-trifluoro-1-(pyridin-3-yl)but-2-en-1-one undergoes a series of transformations, giving 7-trifluoromethyl-1,6-naphthyridine as one of the products. A comparative study of the physicochemical parameters and the crystal structures of amino enones containing a CF<sub>3</sub> group and 2-, 3-, or 4-pyridyl substituents was performed.</p>

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Synthesis, molecular and crystal structures of new amino enones containing trifluoromethyl and 3- or 4-pyridyl substituents

  • 期刊论文

  • 发表日期：

    2025年2月1日

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  • N. S. Boltacheva,
  • P. A. Slepukhin,
  • M. G. Pervova,
  • D. L. Chizhov,
  • V. I. Filyakova,
  • V. N. Charushin

摘要

The reaction of lithium (Z)-1,1,1-trifluoro-4-oxo-4-(pyridin-3-yl)- or (Z)-1,1,1-trifluoro-4-oxo-4-(4-pyridin-4-yl)but-2-en-2-olate with ammonium acetate in glacial AcOH afforded new amino enones containing an amino group geminal to the fluoroalkyl substituent, (Z)-3-amino-4,4,4-trifluoro-1-(pyridin-3-yl)- and (Z)-3-amino-4,4,4-trifluoro-1-(pyridin-4-yl)but-2-en-1-one, respectively. On heating in AcOH under reflux, (Z)-3-amino-4,4,4-trifluoro-1-(pyridin-3-yl)but-2-en-1-one undergoes a series of transformations, giving 7-trifluoromethyl-1,6-naphthyridine as one of the products. A comparative study of the physicochemical parameters and the crystal structures of amino enones containing a CF3 group and 2-, 3-, or 4-pyridyl substituents was performed.