SYNTHESIS AND STRUCTURE OF DIAMINO DERIVATIVES OF PYRANO[3,4-<i>c</i>]PYRIDINES AND 5,6,7,8-TETRAHYDROISOQUINOLINES

Authors

  • Ерванд Г. Пароникян 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., Yerevan 0014
  • Шушаник Ш. Дашян 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., Yerevan 0014
  • Генрих А. Паносян Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014
  • Армен Г. Айвазян Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014
  • Рафаел А. Тамазян Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014

DOI:

https://doi.org/10.1007/4577

Keywords:

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

Abstract

A new and effective method was developed for obtaining diamino derivatives of pyrano[3,4-c]pyridines and 5,6,7,8-tetrahydroisoquinolines 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.

Authors: Ervand G. Paronikyan, Shushanik Sh. Dashyan*, Henrik A. Panosyan, Armen G. Ayvazyan, Rafael A. Tamazyan

Author Biographies

Ерванд Г. Пароникян, 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., Yerevan 0014

зав. лаб., д.х.н. проф.

Шушаник Ш. Дашян, 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., Yerevan 0014

научный сотрудник, к.х.н.

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

зав. лаб., к.х.н.

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

Научный сотрудник

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

зав.  лаб., к. физ.-мат. наук,

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Published

2018-10-01

Issue

Vol. 54 No. 8 (2018)

Section

Original Papers