Synthesis and Spectroscopic Properties of Quinazolinedione Derivatives

El-Baih, Fatma E.M.; Bakari, Safya B. A.; Hijazi, Abdullah

doi:10.4197/sci.16-1.5

Cited by 19 publications

(5 citation statements)

References 23 publications

(34 reference statements)

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“…HCl under stirring. The precipitate was filtered, washed with distilled water, and dried to yield 2,3-dihydro-2-thioxo- [1,2,4] [1,2,4]triazino [3,2-b]quinazolin-3,10dione (15). A mixture of 1 (5 g, 0.028 mol) and ethyl chloroacetate (3.4 g, 0.028 mol) in a mixture of 30 mL pyridine and 30 mL absolute ethanol was refluxed for 5 hr.…”

Section: Synthesis Of 2-5 15 and 19mentioning

confidence: 99%

“…Quinazoline nucleosides were first synthesized by Stout and Robins in 1968 [10] as pyrimidine nucleoside analogs and consequent synthetic studies were contributed by Dunkel and Pfleiderer in the 1990s [11][12][13]. More recently, several quinazoline-2,4-dione nucleosides have been incorporated into oligonucleotides as written or thymidine substitutes to study the binding affinity and base-pairing selectivity [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

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Nucleosides 8 [18]: Ribosylation of Fused Quinazolines—Synthesis of New [1,2,4]Triazolo[5,1-b]- and [1,2,4]Triazino[3,2-b]quinazoline Nucleosides of Fluorescence Interest

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Mosselhi

El‐Shafai

2013

Journal of Chemistry

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1,2,4]Triazolo[5,1-b]-and [1,2,4]triazino [3,2-b] quinazolines have been ribosylated by coupling with 1-O-acetyl-2,3,5-tri-Obenzoyl--D-ribofuranose and by using the silylation method, followed by debenzoylation by methanolic sodium methoxide to afford the corresponding free N-nucleosides. Nucleosides obtained have been identified by their spectral analysis. From the UVvisible and fluorescence studies of some nucleosides synthesized, it is found that they have fluorescence properties. 6 ) 7.20 (d, 2H, aromatic protons, = 8.0 Hz), 7.70 (d, 2H, aromatic protons, = 8.0 Hz), 7.90 (m, 5H, aromatic protons), 11.50 (s, 1H, NH); MS (m/z) = 262 (M + , 70%). Anal. Calcd for C 15 H

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Section: Synthesis Of 2-5 15 and 19mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Nucleosides 8 [18]: Ribosylation of Fused Quinazolines—Synthesis of New [1,2,4]Triazolo[5,1-b]- and [1,2,4]Triazino[3,2-b]quinazoline Nucleosides of Fluorescence Interest

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Mosselhi

El‐Shafai

2013

Journal of Chemistry

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“…More recently, several quinazoline-2,4-dione nucleosides have been incorporated into oligonucleotides as pyrimidine nucleoside substitutes to study the binding affinity and base pairing selectivity (Michel J et al, 1997;Diwan A. R., 1969;T. C. Chien, 2005;F. E. M. El-Baih, 2004;Tun-Cheng CHIEN, 2004).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of New 8-trifluloromethyl Quinazolin-2,4-(3H)-Dione Nucleosides

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2017

IJC

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Synthesis of 8-trifluloromethyl quinazolin-2,4-(1H,3H)-dione 2. which have been ribosylated by coupling with 1-O-acetyl-2,3,5-tri-O-benzoyl--D-ribofuranose 4 by using the silylation method, afforded mixture -and -anomeric of the benzoylated nucleoside derivatives 5 and 6, respectively. Debenzoylation of each of 5 and 6 by sodium metal in dry methanol to afford the corresponding free nucleosides 7 and 8 respectively. The structures of the newly synthesis compounds have been confirmed on the basis of elemental analyses, IR, 1 HNMR, 13 CNMR and Mass spectral data.

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“…Compound 2 is not commercial and should be prepared. There are different reports concerning the preparation of quinazolin‐2,4(1 H ,3 H )‐diones …”

Section: Introductionmentioning

confidence: 99%

Reinvestigation of the Synthesis of Ketanserin (5) and its Hydrochloride Salt (5.HCl) via 3‐(2‐Chloroethyl)‐2,4‐(1H,3H)‐quinazolinedione (2) or Dihydro‐5H‐oxazole(2,3‐b)quinazolin‐5‐one (1)

Fakhraian

Heydary

2013

Journal of Heterocyclic Chem

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The synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) using respectively equimolar amounts of 3‐(2‐chloroethyl)‐2,4‐(1H,3H)‐quinazolinedione (2) with 4‐(parafluorobenzoyl)piperidine (3) and dihydro‐5H‐oxazole(2,3‐b)quinazolin‐5‐one (1) with hydrochloride salt of 4‐(parafluorobenzoyl)piperidine (3.HCl) is reinvestigated. The one‐pot reaction of ethyl‐2‐aminobenzoate with ethyl chloroformate and ethanol amine has afforded 3‐(2‐chloroethyl)‐2,4‐(1H,3H)‐quinazolinedione (2) (86%) that was then refluxed with 4‐(parafluorobenzoyl)piperidine (3) in ethyl methyl ketone in the presence of sodium carbonate to obtain free base of ketanserin (87%). In another attempt, a very pure hydrochloride salt of ketanserin (5.HCl) was synthesized using equimolar amounts of dihydro‐5H‐oxazole(2,3‐b)quinazolin‐5‐one (1) and hydrochloride salt of 4‐(parafluorobenzoyl)piperidine (3.HCl) by a solvent‐less fusion method. Thus, under optimized conditions, 180°C and a reaction time of 30 min, the powder mixture was transformed into glassy crystals that were initially readily soluble in chloroform but were transformed afterwards over time (2 h) to white precipitates (5.HCl) suspended in chloroform with a yield of 72%.

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Synthesis and Spectroscopic Properties of Quinazolinedione Derivatives

Cited by 19 publications

References 23 publications

Nucleosides 8 [18]: Ribosylation of Fused Quinazolines—Synthesis of New [1,2,4]Triazolo[5,1-b]- and [1,2,4]Triazino[3,2-b]quinazoline Nucleosides of Fluorescence Interest

Nucleosides 8 [18]: Ribosylation of Fused Quinazolines—Synthesis of New [1,2,4]Triazolo[5,1-b]- and [1,2,4]Triazino[3,2-b]quinazoline Nucleosides of Fluorescence Interest

Synthesis and Characterization of New 8-trifluloromethyl Quinazolin-2,4-(3H)-Dione Nucleosides

Reinvestigation of the Synthesis of Ketanserin (5) and its Hydrochloride Salt (5.HCl) via 3‐(2‐Chloroethyl)‐2,4‐(1H,3H)‐quinazolinedione (2) or Dihydro‐5H‐oxazole(2,3‐b)quinazolin‐5‐one (1)

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