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Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies

Department of Organic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., 61077 Kharkiv, Ukraine
ChemRar Research and Development Institute, 7 Nobel st., Innovation Center Skolkovo territory, 143026 Moscow, Russia
Faculty of Pharmacy, The National University of Pharmacy, 53 Pushkinska st., 61002 Kharkiv, Ukraine
SSI Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 Nauky Ave, 61001 Kharkov, Ukraine
Chemical Diversity Research Institute, 2A Rabochaya st., Khimki, 141400 Moscow Region, Russia
Author to whom correspondence should be addressed.
Molbank 2019, 2019(4), M1085;
Received: 25 September 2019 / Revised: 12 October 2019 / Accepted: 13 October 2019 / Published: 14 October 2019
(This article belongs to the Special Issue Heterocycle Reactions)
A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, 1H NMR, 13C NMR, LC/MS and single crystal X-ray diffraction. UV/Vis and IR spectra of compounds are described. The presence of a strong intramolecular hydrogen bond between the hydroxy group and the carbonyl oxygen atom of the ester group in methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate is shown. The crystal structure of product was stabilized through intermolecular hydrogen bonds. View Full-Text
Keywords: quinoline; malonic ester; isothiocyanate; condensation quinoline; malonic ester; isothiocyanate; condensation
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Kovalenko, S.M.; Drushlyak, O.G.; Konovalova, I.S.; Mariutsa, I.O.; Kravchenko, D.V.; Ivachtchenko, A.V.; Mitkin, O.D. Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies. Molbank 2019, 2019, M1085.

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