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Synthesis and structure of 4-hydroxy-4-fluoroalkyl-1,4-dihydroimidazo[5,1-c][1,2,4]triazines

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Abstract

Azo coupling of fluorinated 1,3-diketones with 4-ethoxycarbonyl-1H-imidazole-5-diazonium chloride led to the formation of 4-hydroxy-4-polyfluoroalkyl-1,4-dihydroimidazo[5,1-c][1,2,4]triazines. According to the 1H and 19F NMR data, these compounds in solution give rise to ring-chain tautomerism via opening of the C4-N5 bond, which is especially characteristic of dihydroimidazotriazines with a polyfluoroalkyl substituent longer than trifluoromethyl group.

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Correspondence to V. I. Saloutin.

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Original Russian Text © E.V. Shchegol’kov, E.V. Sadchikova, Ya.V. Burgart, V.I. Saloutin, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 4, pp. 586–594.

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Shchegol’kov, E.V., Sadchikova, E.V., Burgart, Y.V. et al. Synthesis and structure of 4-hydroxy-4-fluoroalkyl-1,4-dihydroimidazo[5,1-c][1,2,4]triazines. Russ J Org Chem 45, 572–580 (2009). https://doi.org/10.1134/S1070428009040174

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