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Efficient Synthesis and Some Transformations of 1-Hydrazinyl-5,6,7,8-tetrahydroisoquinolines Involving Rearrangement of the Pyridine Ring

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Abstract

—A procedure was developed for the synthesis of 1-hydrazinyl-3-arylamino-5,6,7,8-tetrahydroisoquinoline- 4-carbonitriles via recyclization of the pyridine ring in 3-amino-2-aryl-1-sulfanylidene-1,2,5,6,7,8- hexahydroisoquinoline-4-carbonitriles by the action of hydrazine hydrate. The recyclization products were converted to new heterocyclic systems, 7,8,9,10-tetrahydro[1,2,4]triazolo[3,4-a]isoquinolines and 1-(3,5-dimethyl- 1H-pyrazol-1-yl)-5,6,7,8-tetrahydroisoquinolines, by reactions with triethyl orthoformate and acetylacetone, respectively. Treatment of 1-hydrazinyl-3-arylamino-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles with sodium azide in acetic acid gave 1-azido-3-arylamino-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles, and azide–tetrazole isomerism of the latter was studied. The state of the azide–tetrazole equilibrium was found to depend on the solvent polarity and substituent nature in the arylamino group. The structure of 5-(2-methoxyanilino)- 7,8,9,10-tetrahydro[1,2,4]triazolo[3,4-a]isoquinoline-6-carbonitrile was confirmed by X-ray analysis, and intermolecular hydrogen bonds were detected in its crystal structure. The synthesized compounds were evaluated for antimicrobial activity.

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Funding

This study was performed in part under financial support by the State Science Committee of the Ministry of Education and Science of Armenia in the framework of research project no. 18T-1D 066.

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Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, Yerevan, Armenia

    E. G. Paronikyan, Sh. Sh. Dashyan, S. S. Mamyan, R. A. Tamazyan & A. G. Ayvazyan

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  1. E. G. Paronikyan
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  2. Sh. Sh. Dashyan
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  3. S. S. Mamyan
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  4. R. A. Tamazyan
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  5. A. G. Ayvazyan
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Correspondence to Sh. Sh. Dashyan.

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The authors declare the absence of conflict of interests.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 9, pp. 1440–1452.

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Paronikyan, E.G., Dashyan, S.S., Mamyan, S.S. et al. Efficient Synthesis and Some Transformations of 1-Hydrazinyl-5,6,7,8-tetrahydroisoquinolines Involving Rearrangement of the Pyridine Ring. Russ J Org Chem 55, 1351–1362 (2019). https://doi.org/10.1134/S1070428019090148

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