Quinoline conjugated imidazopyridine and pyridopyrimidine synthesis in water as highly selective fluoride sensors via a
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ORIGINAL PAPER
Quinoline conjugated imidazopyridine and pyridopyrimidine synthesis in water as highly selective fluoride sensors via a catalyst‑free four‑component reaction Atieh Rezvanian1 · Farzaneh Noorakhtar1 · Ghodsi Mohammadi Ziarani1 · Fatemeh Mahajer1 Received: 12 May 2020 / Accepted: 1 September 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract A green and convenient procedure for the synthesis of quinoline-conjugated imidazopyridines and pyridopyrimidines has been developed by a simple one-pot reaction in the absence of any transition metal catalyst in water. This green process can be readily performed by reacting inexpensive starting materials of 2-chloroquinoline-3-carbaldehyde, malononitrile, 1,1-bis(methylthio)-2-nitroethylene, and diamine in aqueous solution. The present synthesis shows attractive characteristics, such as the use of water as reaction media, convenient one-pot operation, and reduced waste production without the use of any base or metal promoters. The products are purified by crystallization from ethanol, and the process does not involve any hazardous solvent. Also, the fluorescence study of these conjugated systems was also considered, which revealed that they have highly selective sensing of fluoride. Graphic abstract
Keywords Indeno[1,2-b]furan · 2-chloroquinoline-3-carbaldehyde · Quinoline conjugated imidazopyridine and pyridopyrimidine · Nitro ketene dithioacetal · Fluoride sensors
Introduction The quinoline nucleus comprises a class of heterocycles, which has been exploited more immensely than any other nucleus for the development of potent drugs. Since quinoline Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-020-02681-8) contains supplementary material, which is available to authorized users. * Atieh Rezvanian [email protected] 1
Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, PO Box 1993891176, Vanak, Tehran, Iran
is a core structure present in various natural products and pharmaceuticals, compounds containing this scaffold have been extensively used in medicinal chemistry [1–4]. Compounds incorporating quinoline ring system exhibited various biological [5, 6], and pharmaceutical activities e.g. anti-tuberculosis [7], antiplasmodial [8], antibacterial [9, 10], antihistamine [11], antifungal [12], antimalarial [13, 14], anti-HIV [15], anticancer [16], anti-inflammatory [17, 18], anti-hypertensive [19], and antioxidant activities [20]. In addition, the use of quinolines as tyrokinase PDGFRTK inhibitor [21], inositol 50-phosphatase (SH2) [22], DNA gyrase B inhibitors as Mycobacterium tuberculosis [23], and DNA topoisomerase inhibitors [24] were reported.
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Additionally, quinoline derivatives find use in the synthesis of biocides, fungicides, alkaloids, flavoring agents, rubber chemicals, and as an antifoaming agent in refineries [25–28]. Also, quinoline has a privileged scaffold in cancer drug discovery [8].
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