Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies
Author:
Kovalenko Sergiy M.12ORCID, Drushlyak Oleksandr G.3, Konovalova Irina S.4, Mariutsa Illia O.3, Kravchenko Dmitry V.5, Ivachtchenko Alexandre V.2, Mitkin Oleg D.2ORCID
Affiliation:
1. Department of Organic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., 61077 Kharkiv, Ukraine 2. ChemRar Research and Development Institute, 7 Nobel st., Innovation Center Skolkovo territory, 143026 Moscow, Russia 3. Faculty of Pharmacy, The National University of Pharmacy, 53 Pushkinska st., 61002 Kharkiv, Ukraine 4. SSI Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 Nauky Ave, 61001 Kharkov, Ukraine 5. Chemical Diversity Research Institute, 2A Rabochaya st., Khimki, 141400 Moscow Region, Russia
Abstract
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.
Funder
Ministry of Education and Science of the Russian Federation
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