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On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid

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Abstract

The reaction of 2-benzylamino-1,4-naphthoquinone with nitrosylsulfuric acid in acetic acid results in preferential formation of 2,1- and 2,3-heterocyclization products: (E)-4-(hydroxyimino)-2-phenylnaphtho [2,1-d]oxazol-5(4H)-one and 2-phenyl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-dione. In addition, 2-phenylnaphtho[2,1-d]oxazol-4,5-dione and N-(3-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide are also formed. The reaction of 2-benzylamino-3-chloro-1,4-naphthoquinone with nitrosylsulfuric acid in acetic acid gives 3-diazonapthalene-1,2,4(3H)-trione and benzaldehyde.

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Authors and Affiliations

  1. Astaf’ev Krasnoyarsk State Pedagogical University, ul. A. Lebedevoy 89, Krasnoyarsk, 660049, Russia

    L. M. Gornostaev, E. V. Nuretdinova, T. I. Lavrikova, Yu. G. Khalyavina & O. I. Fominykh

  2. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, pr. Akad. Lavrentieva 9, Novosibirsk, 630090, Russia

    Yu. V. Gatilov

  3. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090, Russia

    Yu. V. Gatilov

Authors
  1. L. M. Gornostaev
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  2. E. V. Nuretdinova
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  3. T. I. Lavrikova
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  4. Yu. G. Khalyavina
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  5. O. I. Fominykh
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  6. Yu. V. Gatilov
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Correspondence to L. M. Gornostaev.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 5, pp. 701–708.

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Gornostaev, L.M., Nuretdinova, E.V., Lavrikova, T.I. et al. On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid. Russ J Org Chem 55, 608–614 (2019). https://doi.org/10.1134/S1070428019050051

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  • DOI: https://doi.org/10.1134/S1070428019050051

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