An Efficient One-Step Synthesis of Dihydroquinoline and Its Application as a Fluorescence Sensor for Selective Detection of Copper (II)

Abstract An efficient one-step synthetic pathway to dihydroquinoline (DHQ) and benzodihydroquinoline (BDHQ) derivatives involving 1,2-Michael addition reaction between amino phenol/naphthol and two molecules of methyl propiolate followed by intramolecular cyclization and aromatization using cuprous...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2018-10, Vol.50 (19), p.3886-3890
Main Authors: Hassan, Kamrul, Jonsai, Lamduan, Sittapairoj, Pawitporn, Ajavakom, Vachiraporn, Sukwattanasinitt, Mongkol, Ajavakom, Anawat
Format: Article
Language:English
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Summary:Abstract An efficient one-step synthetic pathway to dihydroquinoline (DHQ) and benzodihydroquinoline (BDHQ) derivatives involving 1,2-Michael addition reaction between amino phenol/naphthol and two molecules of methyl propiolate followed by intramolecular cyclization and aromatization using cuprous iodide as a catalyst was successfully developed. The synthesized DHQ derivatives displayed highly selective fluorescence quenching in the presence of copper(II) with a very low detection limit (LOD for DHQ is 0.20 μM). Moreover, the mechanisms of both formation of the corresponding DHQ and the fluorescence quenching by copper(II) are proposed along with the evidence of X-ray diffraction data.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1609577