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Reactions of polyfluorochalcones with o- and p-phenylenediamines. Synthesis and intramolecular transformations of polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines

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Abstract

Polyfluorochalcones react with o-phenylenediamine in ethanol and 2-propanol in the presence of triethylamine or benzyltriethylammonium chloride (TEBAC) affording polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines. Along with the latter in the presence of triethylamine Michael aza-adducts presumably formed, and at the use of TEBAC in 2-propanol products of intramolecular cyclization and rearrangement of benzo-1,5-diazepines, dihydrobenzimidazo[1,2-a]quinolines were obtained. The reactions of polyfluorochalcones with p-phenylenediamine in ethanol or DMF proceed mostly with the substitution of the para-fluorine atom in the perfluorophenyl rings.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    E. A. Borodina & N. A. Orlova

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  1. E. A. Borodina
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  2. N. A. Orlova
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Correspondence to N. A. Orlova.

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Original Russian Text © E.A. Borodina, N.A. Orlova, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 2, pp. 263–270.

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Borodina, E.A., Orlova, N.A. Reactions of polyfluorochalcones with o- and p-phenylenediamines. Synthesis and intramolecular transformations of polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines. Russ J Org Chem 51, 253–260 (2015). https://doi.org/10.1134/S1070428015020207

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  • DOI: https://doi.org/10.1134/S1070428015020207

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