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

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(1 H )-ones by Smiles rearrangement of the respective oxyacetamides. The structures of the synthesized compounds were studied by NMR spectr...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2018-08, Vol.54 (8), p.804-811
Main Authors: Paronikyan, Ervand G., Dashyan, Shushanik Sh, Panosyan, Henrik A., Ayvazyan, Armen G., Tamazyan, Rafael A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Derivatives
Diffraction
Hydrogen
Hydrogen bonds
NMR spectroscopy
Nuclear magnetic resonance spectroscopy
Organic Chemistry
Pharmacy
Pyridine
Pyridines
Resveratrol
X-ray diffraction
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Summary: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(1 H )-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-1 H -pyrano-[3,4- c ]pyridine-5-carbonitrile. The obtained compounds were also tested for antimicrobial activity.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-018-2353-4