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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 8, pp 804–811 | Cite as

Synthesis and structure of diamino derivatives of pyrano-[3,4-c]pyridines and 5,6,7,8-tetrahydroisoquinolines

  • Ervand G. Paronikyan
  • Shushanik Sh. Dashyan
  • Henrik A. Panosyan
  • Armen G. Ayvazyan
  • Rafael A. Tamazyan
Article
  • 19 Downloads

A new and effective method was developed for obtaining diamino derivatives of pyrano[3,4-c]pyridines and 5,6,7,8-tetrahydro-isoquinolines from 3-cyanopyridin-2(1H)-ones by Smiles rearrangement of the respective oxyacetamides. The structures of the synthesized compounds were studied by NMR spectroscopy and X-ray diffraction analysis. The results of X-ray diffraction studies revealed the presence of intermolecular hydrogen bonds in 6-(benzylamino)-3,3-dimethyl-8-(pyrrolidin-1-yl)-3,4-dihydro-1H-pyrano-[3,4-c]pyridine-5-carbonitrile. The obtained compounds were also tested for antimicrobial activity.

Keywords

pyrano[3,4-c]pyridines 5,6,7,8-tetrahydroisoquinolines antimicrobial activity NMR spectroscopy Smiles rearrangement X-ray structural analysis 

Supplementary material

10593_2018_2353_MOESM1_ESM.pdf (326 kb)
ESM 1 (PDF 325 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Ervand G. Paronikyan
    • 1
  • Shushanik Sh. Dashyan
    • 1
  • Henrik A. Panosyan
    • 2
  • Armen G. Ayvazyan
    • 2
  • Rafael A. Tamazyan
    • 2
  1. 1.A. L. Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical ChemistryNational Academy of Sciences of the Republic of ArmeniaYerevanArmenia
  2. 2.Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical ChemistryNational Academy of Sciences of the Republic of ArmeniaYerevanArmenia

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