Synthesis ( IF 2.2 ) Pub Date : 2018-07-26 , DOI: 10.1055/s-0037-1609577 Anawat Ajavakom 1 , Kamrul Hassan 1 , Lamduan Jonsai 1 , Pawitporn Sittapairoj 1 , Vachiraporn Ajavakom 2 , Mongkol Sukwattanasinitt 1
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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.
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.
中文翻译：
高效一步合成二氢喹啉及其在选择性检测铜（II）的荧光传感器中的应用
摘要
一种有效的一步合成路线，涉及氨基苯酚/萘酚与两个丙酸甲酯分子之间的1,2-迈克尔加成反应，分子内环化和使用碘化亚铜进行芳构化的二氢喹啉（DHQ）和苯并二氢喹啉（BDHQ）衍生物。成功开发。合成的DHQ衍生物在铜（II）的存在下显示出高选择性的荧光猝灭，且检测限非常低（DHQ的LOD为0.20μM）。此外，提出了相应的DHQ的形成机理和铜（II）的荧光猝灭的机理，以及X射线衍射数据的证据。
一种有效的一步合成路线，涉及氨基苯酚/萘酚与两个丙酸甲酯分子之间的1,2-迈克尔加成反应，分子内环化和使用碘化亚铜进行芳构化的二氢喹啉（DHQ）和苯并二氢喹啉（BDHQ）衍生物。成功开发。合成的DHQ衍生物在铜（II）的存在下显示出高选择性的荧光猝灭，且检测限非常低（DHQ的LOD为0.20μM）。此外，提出了相应的DHQ的形成机理和铜（II）的荧光猝灭的机理，以及X射线衍射数据的证据。
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