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Amination of naphthoquinones with azidotrimethylsilane

Aminierung von Naphthochinonen mit Azidotrimethylsilan

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

A new method for the synthesis of aminonaphthoquinones from 1,2- or 1,4-naphthoquinones and azidotrimethylsilane is described. In a similar manner 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone was transformed into 2-amino-3-hydroxy-1,4-naphthoquinone. The mechanism of these transformations and the formation of by-products are discussed.

Zusammenfassung

Eine neue Methode zur Herstellung von Aminonaphthochinonen aus 1,2- oder 1,4-Naphthochinonen und Azidotrimethylsilan wird beschrieben. In analoger Weise wurde 2,3-Epoxy-2,3-dihydro-1,4-naphthochinon in 2-Amino-3-hydroxy-1,4-naphthochinon umgewandelt. Eine mechanistische Deutung dieser Umsetzung und die Bildung von Nebenprodukten wird diskutiert.

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Authors and Affiliations

  1. Department of Chemistry, E. Kardelj University, YU-61000, Ljubljana, Yugoslavia

    Breda Husu, Zdenka Kadunc & Miha Tišler

  2. Department of Organic Chemistry, Prague Institute of Chemical Technology, Praha, Czechoslovakia

    Stanislav Kafka

Authors
  1. Breda Husu
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  2. Stanislav Kafka
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  3. Zdenka Kadunc
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  4. Miha Tišler
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Husu, B., Kafka, S., Kadunc, Z. et al. Amination of naphthoquinones with azidotrimethylsilane. Monatsh Chem 119, 215–222 (1988). https://doi.org/10.1007/BF00809595

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  • DOI: https://doi.org/10.1007/BF00809595

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