Molbank (Nov 2019)

2,2’-[(1,4-Dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene)]bis(quinoline-3-carboxylic acid)

  • Joanna Fedorowicz,
  • Karol Gzella,
  • Paulina Wiśniewska,
  • Jarosław Sączewski

Journal volume & issue
Vol. 2019, no. 4
p. M1093


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The title compound, 2,2’-[(1,4-dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene)]bis(quinoline-3-carboxylic acid) was synthesized from isoxazolo[3,4-b]quinolin-3(1H)-one and dimethyl acetylenedicarboxylate (DMAD) via a double aza-Michael addition followed by [1,3]-H shifts. The product was characterized by infrared and nuclear magnetic resonance spectroscopy, as well as elemental analysis and high-resolution mass spectrometry (HRMS). The proposed reaction mechanism was rationalized by density functional theory (DFT) calculations.