Reaction of 1-substituted 3-aminoquinolinediones with isocyanic and isothiocyanic acid

Mrkvička, Vladimír; Rudolf, Ondřej; Lyčka, Antonı́n; Klásek, Antonı́n

doi:10.1016/j.tet.2011.02.002

Cited by 10 publications

(7 citation statements)

References 10 publications

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“…Previous studies have shown the easy debenzylation of compounds bearing a benzyl group in position 3. 9,11 Compounds 5a, 5b and 5d are products of a molecular rearrangement of compounds 2, in which the quinolone ring opens to form an intermediate isocyanate, before subsequently closing and forming a quinazoline ring. Compounds 5 are structurally similar to compounds prepared in previous studies 9 and their structure was established on the basis of 2D-NMR experiments (see Table 2).…”

Section: Resultsmentioning

confidence: 99%

“…Under these conditions, more types of new heterocycles were prepared, e.g., thioureidooxindoles, spiro-oxindoles, dihydroimidazoquinolones and their sulfur analogues. 9 In order to discover the influence of other substituents in the amine molecule, we chose to use ethanolamine, as it is an as easily available and inexpensive compound. In our earlier paper, 10 we described its reaction with 3-chloroquinoline-2,4-diones.…”

Section: Introductionmentioning

confidence: 99%

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Completely dissimilar: The reactivity of 1-unsubstituted 3-chloroquinoline-2,4-diones with ethylene diamine and ethanolamine to form new molecular rearrangements

Klásek¹,

Lyčka²,

Rouchal³

2020

Arkivoc

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3-Chloroquinoline-2,4-diones react with ethanolamine to give 3-hydroxyethylaminoquinoline-2,4-diones. By reacting with isothiocyanic acid, these compounds cyclize to form thioxoimidazo derivatives. If a benzyl group is attached to carbon atom C-3, it is cleaved off. Simultaneously, molecular rearrangement proceeds through the formation of compounds with quinazoline skeletons. However, when using ethylene diamine, the compounds are subject to new types of molecular rearrangement leading to the formation of new quinazoline derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Completely dissimilar: The reactivity of 1-unsubstituted 3-chloroquinoline-2,4-diones with ethylene diamine and ethanolamine to form new molecular rearrangements

Klásek¹,

Lyčka²,

Rouchal³

2020

Arkivoc

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“…The group of reactive compounds including an amino group (especially α-aminoketones with respect to their easily conversion) belongs to various heterocycles [ 1 ]. Suitable compounds of this type are 3-aminoquinoline-2,4-diones, which is our particular area of interest [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ]. Even if the occurrence of these compounds in the relevant literature was early rather than rare [ 16 , 17 ], we managed to prepare 3-aminoderivatives using 3-chloroquinolinediones and ammonium salts or primary amines [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

“…We found that 3-aminoquinoline-2,4-diones were subject to molecular rearrangements after their reaction with urea [ 3 , 4 , 5 ], nitrourea [ 6 , 7 ], isocyanates [ 8 ], isothiocyanates [ 9 , 10 , 11 ], isothiocyanic acid [ 12 , 13 , 15 ], and isocyanic acid [ 13 ], creating a broad palette of new heterocyclic compounds, e.g., imidazo[1,5- c ]quinazoline-3,5-diones, 3-(3-acylureido)-2,3-dihydro-1 H -indol-2-ones, 4-alkylidene-1’ H -spiro[imidazolidine-5,3’-indole]-2,2’-diones and spiro-linked imidazoline-2-thiones.…”

Section: Introductionmentioning

confidence: 99%

Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid

Klásek

Lyčka

Křemen

et al. 2022

IJMS

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New tetrahydropyrazino[2,3-c]quinolin-5(6H)-ones were prepared from 3-chloroquinoline-2,4(1H,3H)-diones and ethylene diamine. In their reaction with HNCO, an unprecedented molecular rearrangement produced new types of hydantoin derivatives. All prepared compounds were characterized on the basis of their 1H, 13C, and 15N NMR and ESI mass spectra and some were authenticated by X-ray analysis of single crystalline material. A proposed mechanism for rearrangement is discussed in this essay. The CDK and ABL inhibition activity as well as in vitro cytotoxicity of the prepared compounds was also tested.

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“…Imidazo[1,5-c]quinazoline-3,5-dione derivatives, obtained during reaction 3-aminoquinolinediones with urea as a result of rearrangement [ 5 , 6 ], can also have biological activity. Unfortunately, they are sparingly soluble and because of that fact their application is difficult.…”

Section: Introductionmentioning

confidence: 99%

Esters with imidazo [1,5-c] quinazoline-3,5-dione ring spectral characterization and quantum-mechanical modeling

et al. 2017

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1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione reacts with ethyl bromoacetate under mild conditions to give 2-(ethoxycarbonylmethyl)-1-phenyl-6H-imidazo[1,5-c]quinazoline-3,5-dione (MEPIQ) and next 2,6-bis(ethoxycarbonylmethyl)-1-phenylimidazo[1,5-c]quinazoline-3,5-dione (BEPIQ). The products were isolated at high yield and identified on the basis of IR, 1H- and 13C-NMR, UV spectroscopy, and X-ray crystallography. Diester (BEPIQ) can be presented by 16 possible pair of enantiomers. Only one pair of them is the most stable and crystallizes which is shown crystallographic research. Based on quantum-mechanical modeling, with the use of DFT method, which conformers of mono- and diester and why they were formed was explained. It was calculated that 99.93% of the monoester (MEPIQ) is formed at position No. 2 and one pair of the monoester conformers, from six possible, has the largest share (51.63%). These results afforded to limit the number of diester conformers to eight. Unfortunately, the quantum-mechanical calculations performed that their shares are similar. Further quantum-mechanical modeling showed that conformers are able to undergo mutual transformations. As a result only one pair of diester conformers forms crystals. These conformers have substituents in trans position and these substituents are located parallel to imidazoquinazoline ring. This allows for the denser packing of the molecules in the unit cell.Electronic supplementary materialThe online version of this article (doi:10.1007/s00894-017-3284-1) contains supplementary material, which is available to authorized users.

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Reaction of 1-substituted 3-aminoquinolinediones with isocyanic and isothiocyanic acid

Cited by 10 publications

References 10 publications

Completely dissimilar: The reactivity of 1-unsubstituted 3-chloroquinoline-2,4-diones with ethylene diamine and ethanolamine to form new molecular rearrangements

Completely dissimilar: The reactivity of 1-unsubstituted 3-chloroquinoline-2,4-diones with ethylene diamine and ethanolamine to form new molecular rearrangements

Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid

Esters with imidazo [1,5-c] quinazoline-3,5-dione ring spectral characterization and quantum-mechanical modeling

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