2,2’-[(1,4-Dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene)]bis(quinoline-3-carboxylic acid)
1
Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, Gdańsk 80-416, Poland
2
Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, Gdańsk 80-416, Poland
*
Author to whom correspondence should be addressed.
Molbank 2019, 2019(4), M1093; https://doi.org/10.3390/M1093
Received: 27 October 2019 / Revised: 19 November 2019 / Accepted: 19 November 2019 / Published: 21 November 2019
(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)
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.
Keywords:
[1,3]-H shift; aza-Michael addition; DFT calculations; dimethyl acetylenedicarboxylate; isoxazolo[3,4-b]quinolin-3(1H)-one
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MDPI and ACS Style
Fedorowicz, J.; Gzella, K.; Wiśniewska, P.; Sączewski, J. 2,2’-[(1,4-Dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene)]bis(quinoline-3-carboxylic acid). Molbank 2019, 2019, M1093.
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