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Russian Journal of Organic Chemistry

, Volume 55, Issue 5, pp 608–614 | Cite as

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

  • L. M. GornostaevEmail author
  • E. V. Nuretdinova
  • T. I. Lavrikova
  • Yu. G. Khalyavina
  • O. I. Fominykh
  • Yu. V. Gatilov
Article
  • 23 Downloads

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.

Keywords

2-benzylamino-1,4-naphthoquinone hydroxyimidazole naphtho-1,2-oxazole oximes 2,3-diazido-1,4-naphthoquinone nitrosylsulfuric acid 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • L. M. Gornostaev
    • 1
    Email author
  • E. V. Nuretdinova
    • 1
  • T. I. Lavrikova
    • 1
  • Yu. G. Khalyavina
    • 1
  • O. I. Fominykh
    • 1
  • Yu. V. Gatilov
    • 2
    • 3
  1. 1.Astaf’ev Krasnoyarsk State Pedagogical UniversityKrasnoyarskRussia
  2. 2.Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RASNovosibirskRussia
  3. 3.Novosibirsk State UniversityNovosibirskRussia

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