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Issue 18, 2017
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Synthesis of 2-amino- and 2-arylazoazulenes via nucleophilic aromatic substitution of 2-chloroazulenes with amines and arylhydrazines

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Abstract

The SNAr reaction of 2-chloroazulene derivative 1 with ethoxycarbonyl groups at the 1,3-positions of the azulene ring with several amines afforded the corresponding 2-aminoazulenes 3–9 in excellent yields. 2-Chloroazulene (2) without the electron-withdrawing groups reacted with highly nucleophilic cyclic amines (i.e., morpholine, piperidine and pyrrolidine) under the high-temperature conditions in a sealed tube to produce the corresponding 2-aminoazulenes 10–12 in good yields. 2-Aminoazulenes 10–14 without the electron-withdrawing groups were also obtained in good yields by the treatment of compounds 3–7 with 100% H3PO4, but in the cases of the reaction of 8 and 9 with a secondary amine function, the decomposition of the products resulted. The synthesis of 2-arylazoazulenes 15–18 was also established via the SNAr reaction of 1 with arylhydrazines. The optical and electrochemical properties of the 2-arylazoazulene derivatives were examined by UV/Vis spectroscopy, theoretical calculations and voltammetric experiments.

Graphical abstract: Synthesis of 2-amino- and 2-arylazoazulenes via nucleophilic aromatic substitution of 2-chloroazulenes with amines and arylhydrazines

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Publication details

The article was received on 21 Mar 2017, accepted on 11 Apr 2017 and first published on 12 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00691H
Citation: Org. Biomol. Chem., 2017,15, 3917-3923
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    Synthesis of 2-amino- and 2-arylazoazulenes via nucleophilic aromatic substitution of 2-chloroazulenes with amines and arylhydrazines

    T. Shoji, S. Sugiyama, T. Araki, A. Ohta, R. Sekiguchi, S. Ito, S. Mori, T. Okujima and M. Yasunami, Org. Biomol. Chem., 2017, 15, 3917
    DOI: 10.1039/C7OB00691H

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