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

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

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1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)608-614
Number of pages7
JournalRussian Journal of Organic Chemistry
Volume55
Issue number5
DOIs
Publication statusPublished - 1 May 2019

Keywords

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

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