Solvent and catalyst-free synthesis of some new aminonaphthoquinones from lawsone, ninhydrin and heteroaryl amines
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Solvent and catalyst‑free synthesis of some new aminonaphthoquinones from lawsone, ninhydrin and heteroaryl amines Abolfazl Olyaei1 · Neda Taheri1 · Mahdieh Sadeghpour2 Received: 18 September 2020 / Accepted: 9 November 2020 © Springer Nature B.V. 2020
Abstract An efficient and easy method has been developed for the preparation of some new aminonaphthoquinone derivatives from a one-pot three-component condensation of 2-hydroxy-1,4-naphthoquinone, ninhydrin and heteroaryl amines under catalyst and solvent-free conditions at 75 °C. The protocol describes in situ generated imine as intermediate from the condensation reaction of ninhydrin with heteroaryl amines followed by the addition of 2-hydroxynaphthalene-1,4-dione to the imine, afforded the desired products. The operational simplicity of the procedure, shorter reaction times, simple workup procedure, clean reaction, easy purification of products by nonchromatographic methods, environmentally friendly conditions and high yields make this method much attractive. Keywords Lawsone · Heteroaryl amine · Aminoalkylation · Naphthoquinone · Ninhydrin
Introduction 2-Hydroxy-1,4-naphthoquinone, or lawsone, or hennotannic acid, is one of the simplest naturally occurring naphthoquinones. This red–orange pigment can be obtained from the extract of dried powdered leaves of henna, a branched shrub or small tree with grayish-brown bark. Lawsone is traditionally used for coloring hair and dying nails and skin [1, 2] and served as an inspiration for the development of new bioactive compounds [3]. Besides, it has several other uses including antiaging Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04325-2) contains supplementary material, which is available to authorized users. * Abolfazl Olyaei [email protected] 1
Department of Chemistry, Payame Noor University (PNU), PO BOX 19395‑4697, Tehran, Iran
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Department of Chemistry, Takestan Branch, Islamic Azad University, Takestan, Iran
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additive to vulcanized natural rubber [4], skin protection from ultraviolet radiation [5], oxidation of chlorinated compounds [6] and corrosion inhibition for steel [7]. Furthermore, it is a sensitive colorimetric and electrochemical sensor for anions, such as cyanide, acetate, fluoride and dihydrogen phosphate (DHP) in acetonitrile [8]. 1,2,3-Indanetrione or ninhydrin was first reported in 1910 by Siegfried Ruhemann [9]. Ninhydrin reaction is traditionally applied for the detection of amino acids, peptides and proteins to agricultural and biomedical sciences [10, 11]. Besides, it is considered to be a very important applications in environmental chemistry, clinical chemistry, food chemistry and forensic sciences [12–16]. The C-2 position of this compound, which is situated between two other carbonyl groups, is more reactive toward nucleophiles. Considering the importance of ninhydrin as a building block in organic synthesis, there are many published articles on the different reactions o
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