2009
DOI: 10.1016/j.tet.2009.09.048
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Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates

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Cited by 12 publications
(10 citation statements)
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“…The assignment of resonances in the NMR spectra was based on the chemical shift theory, multiplicities, intensity, and a comparison with similar spectral characteristics of structurally related compounds [29][30][31][32][33][34][35][36][37][38][39][40][41]. The assignment of resonances in the NMR spectra was based on the chemical shift theory, multiplicities, intensity, and a comparison with similar spectral characteristics of structurally related compounds [29][30][31][32][33][34][35][36][37][38][39][40][41].…”
Section: Resultsmentioning
confidence: 99%
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“…The assignment of resonances in the NMR spectra was based on the chemical shift theory, multiplicities, intensity, and a comparison with similar spectral characteristics of structurally related compounds [29][30][31][32][33][34][35][36][37][38][39][40][41]. The assignment of resonances in the NMR spectra was based on the chemical shift theory, multiplicities, intensity, and a comparison with similar spectral characteristics of structurally related compounds [29][30][31][32][33][34][35][36][37][38][39][40][41].…”
Section: Resultsmentioning
confidence: 99%
“…1 H-NMR and 13 C-NMR spectral data. The assignment of resonances in the NMR spectra was based on the chemical shift theory, multiplicities, intensity, and a comparison with similar spectral characteristics of structurally related compounds [29][30][31][32][33][34][35][36][37][38][39][40][41].The starting compounds-carbohydrazides 2a,b-were synthesized by the reaction of dicarboxylic acid esters and hydrazine hydrate in boiling 2-propanol with 78 −80% yields as illustrated in Scheme 1. Azole derivatives can be obtained by the interaction of carbohydrazides and diketones.…”
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confidence: 99%
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“…The assignment of resonances in the NMR spectra was based on the chemical shift theory, using previously determined [23] and published [24] increments of substituents, signal intensity arguments, and multiplicities, and a comparison with structurally related compounds [20,[25][26][27][28][29][30][31][32][33][34][35][36][37][38]. The DEPT ( 13 C) and 1 H/ 13 C 2D (HETCOR) methods were used in some cases.…”
Section: Introductionmentioning
confidence: 99%
“…Furthermore, through the reaction of 3-aminoquinoline-2,4-diones with isothiocyanates, 1,2,3,3a,5,9b-hexahydro-9b-hydroxy-2-thioxoimidazo [4,5-c]quinolin-4-ones were obtained [9] [10]. Molecular rearrangement of these addition products in boiling AcOH or concentrated HCl solution yields products displaying quite exceptional structural diversity, including imidazoquinazolines, oxindoles, spiro[imidazo-oxindoles], indolylureas, imidazolones, 1,3-bis[2-(imidazolyl)phenyl]ureas, 2-thioxo-1'H-spiro[imidazoline-5,3'-indol]-2'-ones, 1H-imidazole-2(3H)-thiones, 1,3-bis[2-(2,3-dihydro-2-thioxo-1H-imidazol-5-yl)phenyl]ureas, and N-[2-(2,3-dihydro-2-thioxo-1H-imidazol-4-yl)phe-nyl]acetamides [8 -10].…”
mentioning
confidence: 99%