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Synthesis and Properties of 4,6-Dimethyl-5-pentyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile and 3-Amino-4,6-dimethyl-5-pentylthieno[2,3-b]pyridines

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Abstract

The reaction of 3-pentylpentane-2,4-dione with cyanothioacetamide afforded 4,6-dimethyl-5-pentyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile. Alkylation of the latter led to the formation of 2-alkylsulfanyl-4,6-dimethyl-5-pentylpyridine-3-carbonitriles or 3-amino-4,6-dimethyl-5-pentylthieno[2,3-b]pyridines, depending on the alkylating agent and reaction conditions. The structures of the key compounds were proved by 2D NMR spectroscopy and X-ray analysis. Biological activity of the synthesized compounds was evaluated in silico. Some compounds were experimentally found to stimulate growth of sunflower seedlings.

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Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 4.5547.2017/8.9, V.V. Dotsenko, I.V. Aksenova; project no. 4.1196.2017/4.6, N.A. Aksenov). Biological studies were performed in the framework of state assignment of the Ministry of Science and Higher Education of the Russian Federation (project no. 075-00376-19-00) and research project no. 0686-2019-0013.

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Correspondence to D. S. Buryi.

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Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 8, pp. 1182–1194.

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Buryi, D.S., Dotsenko, V.V., Aksenov, N.A. et al. Synthesis and Properties of 4,6-Dimethyl-5-pentyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile and 3-Amino-4,6-dimethyl-5-pentylthieno[2,3-b]pyridines. Russ J Gen Chem 89, 1575–1585 (2019). https://doi.org/10.1134/S1070363219080061

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