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

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Department of Organic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., 61077 Kharkiv, Ukraine
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ChemRar Research and Development Institute, 7 Nobel st., Innovation Center Skolkovo territory, 143026 Moscow, Russia
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Faculty of Pharmacy, The National University of Pharmacy, 53 Pushkinska st., 61002 Kharkiv, Ukraine
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SSI Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 Nauky Ave, 61001 Kharkov, Ukraine
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Chemical Diversity Research Institute, 2A Rabochaya st., Khimki, 141400 Moscow Region, Russia
*
Author to whom correspondence should be addressed.
Molbank 2019, 2019(4), M1085; https://doi.org/10.3390/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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