One-pot synthesis and structural elucidation of polyfunctionalized quinoxalines and their use as chromogenic chemosensors for ionic species

• Published in: Journal of molecular structure Vol. 1195; pp. 936 - 943
• Main Authors: da Silva, Lilian C., Lindner, Alexandra, Cavalcanti, Lívia N., da Costa, Erivaldo P., Azevedo, Mireia M., Araújo, Renata M., de Freitas, Gutto R.S., de Souza, Miguel A.F., Machado, Vanderlei G., Menezes, Fabrício G.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.11.2019
• Subjects: Ascorbic acid; Chromogenic chemosensors; Ion sensing; Quinoxaline; Structural elucidation; Quinoxaline; Structural elucidation; Ascorbic acid; Ion sensing; Chromogenic chemosensors
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2019.06.025

The one-pot synthesis of nine novel polyfunctionalized quinoxaline derivatives starting from l-ascorbic acid is described. Reaction products were obtained in moderate to good yields (65–84%) for an interesting scope of aldehydes after four synthetic transformations. Structural characterization of the molecules was performed by combined NMR (1H, 13C, DEPT-135 COSY and HSQC) techniques, infrared spectroscopy and theoretical calculations. Two selected target-compounds were evaluated as chromogenic chemosensors for ionic species in solution. One of the compounds was effective in the selective detection of Cu2+ in methanol-water 4:1 v/v solution. The other compound was applied as a chemosensor for F− in DMSO and aqueous DMSO solution. Binding mechanisms were proposed based on spectroscopic and theoretical data. [Display omitted] •The one-pot synthesis of polyfunctionalized quinoxaline derivatives is described.•Two selected compounds were evaluated as chemosensors for ions.•Structural analysis using experimental and theoretical techniques.•Compounds 1a and 1b, respectively, were selective for Cu2+ and F−.•Binding models were proposed based on spectroscopic and computational data.