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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. A. L. Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., 0014, Yerevan, Armenia

    Ervand G. Paronikyan & Shushanik Sh. Dashyan

  2. Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., 0014, Yerevan, Armenia

    Henrik A. Panosyan, Armen G. Ayvazyan & Rafael A. Tamazyan

Authors
  1. Ervand G. Paronikyan
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  2. Shushanik Sh. Dashyan
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  3. Henrik A. Panosyan
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  4. Armen G. Ayvazyan
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  5. Rafael A. Tamazyan
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Correspondence to Shushanik Sh. Dashyan.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(8), 804–811

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Paronikyan, E.G., Dashyan, S.S., Panosyan, H.A. et al. Synthesis and structure of diamino derivatives of pyrano-[3,4-c]pyridines and 5,6,7,8-tetrahydroisoquinolines. Chem Heterocycl Comp 54, 804–811 (2018). https://doi.org/10.1007/s10593-018-2353-4

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