One Pot Synthesis of 7-[1, 2-Dihydro-4-Hydroxy-1-Methyl/Phenyl-2-OXO-3-Quinolinyl]-5, 7-Dihydro-5-Methyl/Phenyl-6H-[1]-Benzo Pyrano [3, 2-c] Quinolin-6-Ones

Rao, V. S.; Darbarwar, M.

doi:10.1080/00397918808082369

Cited by 12 publications

(5 citation statements)

References 4 publications

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“…Surprisingly, on attempting to prepare 4-hydroxy-2-quinolone 1g from 2-hydroxyaniline ( 9 ) and diethyl malonate ( 10 ) in polyphosphoric acid (PPA) according to the procedure described in reference [28], compound 11 was obtained in 80% yield (Scheme 4). Similarly, reaction of 11 with 4 under the same conditions produced compound 12 in 85% yield.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

et al. 2019

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Section: Resultsmentioning

confidence: 99%

“…1,6-Disubstituted-quinoline-2,4-(1 H ,3 H )-diones 1a – f were prepared according to the literature [28,29]. 2,3-Dichloropyrazine ( 2 ) and ( E )-1,2-dibenzoylethene ( 4 ) (Aldrich, Munich, Germany) were used as received.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

et al. 2019

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“…1,6-Disubstituted-quinoline-2,4-(1 H ,3 H )-diones 1a–g were prepared according to the literature [ 35 , 36 ] whereas carbaldehydes 5a , 5b , 5c–f and 5g were synthesized according to the literature [ 37 – 40 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 3,3′-methylenebis(4-hydroxyquinolin-2(1H)-ones) of prospective anti-COVID-19 drugs

et al. 2020

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During formylation of 2-quinolones by DMF/Et 3 N mixture, the unexpected 3,3′-methylenebis(4-hydroxyquinolin-2(1H)ones) were formed. The discussed mechanism was proved as due to the formation of 4-formyl-2-quinolone as intermediate. Reaction of the latter compound with the parent quinolone under the same reaction condition gave also the same product. The structure of the obtained products was elucidated via NMR, IR and mass spectra. X-ray structure analysis proved the anti-form of the obtained compounds, which were stabilized by the formation hydrogen bond. Molecular docking calculations showed that most of the synthesized compounds possessed good binding affinity to the SARS-CoV-2 main protease (M pro) in comparable to Darunavir.

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“…4-Hydroxyquinoline derivatives 1a-c were prepared according to the literature [30][31][32]. Ethyl bromoacetate (2) and isothiocyanate derivatives were bought from Aldrich and used as received.…”

Section: Starting Materialsmentioning

confidence: 99%

Regioselective formation of new 3- S -alkylated-1,2,4-triazole-quinolones

Aly

Elaziz

Elshaier

et al. 2021

Journal of Sulfur Chemistry

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Regioselective synthesis of quinolone-1,2,4-triazoles was established starting from 4-hydroxyquinol-2-ones. The strategy started by the reaction of ethyl bromoacetate with 4-hydroxyquinoline to give the corresponding ethyl oxoquinolinyl acetates, which reacted with hydrazine hydrate to afford the hydrazide derivatives. Subsequently, hydrazides reacted with isothiocyanate derivatives to give the corresponding acyl thiosemicarbazides. Finally, subjecting the thiosemicarbazide derivatives with ethyl bromoacetate, reaction underwent internal cyclization and alkylation processes. Alkylation occurred regioselectivity to sulfur atom of thione group and not to amino group. Thus 3-S-1,2,4-triazole-quinolones were obtained in good yields. The structure of the obtained compounds was proved by different spectroscopic together with elemental analysis and Xray crystallography.

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One Pot Synthesis of 7-[1, 2-Dihydro-4-Hydroxy-1-Methyl/Phenyl-2-OXO-3-Quinolinyl]-5, 7-Dihydro-5-Methyl/Phenyl-6H-[1]-Benzo Pyrano [3, 2-c] Quinolin-6-Ones

Cited by 12 publications

References 4 publications

Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

Synthesis of 3,3′-methylenebis(4-hydroxyquinolin-2(1H)-ones) of prospective anti-COVID-19 drugs

Regioselective formation of new 3- S -alkylated-1,2,4-triazole-quinolones

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