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Alkylation of C- and N-aminotriazoles with α-iodoketones

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Abstract

C- and N-Amino-1,2,4-triazoles react with 1-iodopropan-2-one in the absence of bases and phasetransfer catalysts (40°C, 9-12 h) to furnish 3-amino-1,4-bis(2-oxo-propyl)-4H-1,2,4-triazolium triiodide and 4-amino-1-(2-oxopropyl)-4H-1,2,4-triazolium iodide. The alkylation of 1,2,4-triazol-4-amine with 1-iodopropan-2-one and 1,3-diiodopropan-2-one in the presence of elemental iodine led to the formation of 4-amino-1-(2-oxopropyl)-4H-1,2,4-triazolium triiodide and 2-oxopropane-1,3-diylbis(4-amino-4H-1,2,4-triazolium) bis(triiodide). Triiodides are oily fluids possessing electric conductivity of 1.1 × 10−3 Ω m−1 opening the route to new types of electroconducting ionic liquids.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    L. G. Shagun, I. A. Dorofeev, N. O. Yarosh, L. V. Zhilitskaya, L. I. Larina & M. G. Voronkov

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  1. L. G. Shagun
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  2. I. A. Dorofeev
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  3. N. O. Yarosh
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  4. L. V. Zhilitskaya
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  5. L. I. Larina
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  6. M. G. Voronkov
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Correspondence to L. G. Shagun.

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Original English Text © L.G. Shagun, I.A. Dorofeev, N.O. Yarosh, L.V. Zhilitskaya, L.I. Larina, M.G. Voronkov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1693–1696.

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Shagun, L.G., Dorofeev, I.A., Yarosh, N.O. et al. Alkylation of C- and N-aminotriazoles with α-iodoketones. Russ J Org Chem 49, 1676–1679 (2013). https://doi.org/10.1134/S1070428013110195

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  • DOI: https://doi.org/10.1134/S1070428013110195

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