Synthesis of new 2-aminocarbohydrate-1,4-naphthoquinone derivatives promoted by ultrasonic irradiation

In this report we describe the ultrasound-accelerated synthesis of new naphthoquinone derivatives 6a-f and 7a-c, which possess an aminocarbohydrate chain at the C-2 position of the quinone ring. This novel type of 1,4-naphthoquinone derivative has been synthesized under mild conditions by the reacti...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2011, Vol.22 (1), p.187-193
Main Authors: Franco, Caroline F. J., Jordão, Alessandro K., Ferreira, Vitor F., Pinto, Angelo C., Souza, Maria C. B. V. de, Resende, Jackson A. L. C., Cunha, Anna C.
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:In this report we describe the ultrasound-accelerated synthesis of new naphthoquinone derivatives 6a-f and 7a-c, which possess an aminocarbohydrate chain at the C-2 position of the quinone ring. This novel type of 1,4-naphthoquinone derivative has been synthesized under mild conditions by the reaction of 1,4-naphthoquinone (8a) or methoxylapachol (8b) with different aminocarbohydrates 9a-d. Characterization of all substances was confirmed by one- and two-dimensional nuclear magnetic resonance (NMR) techniques (¹H, 13C-APT, cosy-¹H vs. ¹H and HETCOR ¹J CH) and by high-resolution electrospray ionization mass spectrometry (HR ESI MS).
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50532011000100026