Synthesis of 3-substituted 2-aminonaphtho[2,3-b]furan-4,9-diones from 2-hydroxy-1,4-naphthoquinone and nitroalkenes

Manoj R. Zanwar, Veerababurao Kavala, Sachin D. Gawande, Chun Wei Kuo, Ting Shen Kuo, Mei Ling Chen, Chiu Hui He, Ching Fa Yao

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Abstract

The efficient base-catalyzed synthesis of 3-substituted 2-aminonaphtho[2,3-b]furan-4,9-dione derivatives from readily available precursors such as 2-hydroxy-1,4-naphthoquinone and nitroalkenes under aqueous conditions is described. Interesting features of this methodology are the conversion of a nitro functionality into an amino functionality in the absence of a reducing agent and the development of a three component reaction for accessing the same product from an aldehyde, 2-hydroxy-1,4-naphthoquinone and nitromethane. 3-Substituted 2-aminonaphtho[2,3-b]furan-4,9-diones have been synthesized from 2-hydroxy-1,4-naphthoquinone and nitro alkenes under aqueous conditions. In this methodology, a nitro moiety is converted into an amino functionality in the absence of a reducing agent. The same products were obtained from a three-component reaction involving aldehydes, 2-hydroxy-1,4-naphthoquinone, and nitromethane.

Original languageEnglish
Pages (from-to)8288-8298
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number36
DOIs
Publication statusPublished - 2013 Dec 1

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Keywords

  • Amines
  • Green chemistry
  • Multicomponent reactions
  • Nitroalkenes
  • Quinones

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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