The simple synthesis of quinazoline-2,4-dione derivatives using Boc strategy

Li, Xu Qin

doi:10.1016/j.cclet.2009.05.001

Cited by 10 publications

(2 citation statements)

References 13 publications

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“…Quinazolinediones are an important class of nitrogen-containing heterocycles in medicinal chemistry with a broad range of bioactivities, such as antihypertensive, , antidiabetic, antimicrobial, , antimalarial, , and anticancer activities. − Structures shown in Figure are representative examples of commercial drugs or biologically active compounds and natural products containing the quinazoline-2,4-dione core. − Among them, Zenarestat is a therapeutic agent against diabetic neuropathy. Due to the importance of quinazoline-2,4-diones in medicinal chemistry, various synthetic methods have been reported to construct this core. − The representative strategies for the construction of quinazoline-2,4-diones have been summarized in the introduction part of our previous article . The key precursor reagents such as urea, triphosgene, CO, CO 2 , dimethylformamide (DMF), 1,1′-carbonyldiimidazole (CDI), and KOCN are crucial to the introduction of the 2-position carbonyl group.…”

Section: Introductionmentioning

confidence: 99%

DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate

et al. 2020

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The one-pot synthesis of quinazoline-2,4-diones was developed in the presence of 4-dimethylaminopyridine (DMAP) by metal-free catalysis. The commercially available (Boc)2O acted as a key precursor in the construction of the 2-position carbonyl of quinazolinediones. The p-methoxybenzyl (PMB)-activated heterocyclization could smoothly proceed at room temperature instead of the microwave condition. This strategy is compatible with a variety of substrates with different functional groups. Furthermore, this protocol was utilized to smoothly prepare Zenarestat with a total yield of 70%.

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Section: Introductionmentioning

confidence: 99%

DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate

et al. 2020

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“…Quinazoline-2,4(1H,3H)-dione moiety could be constructed by cyclization of 2-aminobenzonitrile with DMF (Rasal and Yadav, 2016), the reaction of CO 2 and 2-aminobenzonitriles (Ma et al, 2013), carbonylation and then cyclization of anthranilamide (Li, 2009), and treatment of substituted anthranilic acid with potassium cyanate (El-Brollosy, 2007). However, quinazoline-2,4(1H,3H)-diones can be synthesized via many methods but most of them suffer from structure diversity and scope expanding.…”

Section: Introductionmentioning

confidence: 99%

Preparation of skeletally diverse quinazoline-2,4(1H,3H)-diones using Na₂SiO₃/SnFe₂O₄ catalytic system through a four-component reaction

Ayambekam

Ghashang

2020

Main Group Metal Chemistry

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Sodium silicate with the formula of Na2SiO3 was used for the four-component reaction of ketones, aldehydes and cyanoacetamide. The effect of SnFe2O4 nano-particles on the catalytic potential of Na2SiO3 was investigated. The desired products synthesized by this method are 5-amino-7-aryl-2,4-dioxo-2,3,4,4a,7,7a,8,9,10,11-decahydro-1H-benzo[i]quinazoline-6-carbonitriles, 5-amino-2,4-dioxo-7-aryl-1,2,3,4,4a,7,7a,8,10,11-decahydropyrano[3,4-i] quinazoline-6-carbonitrile, 5-amino-9-methyl-2,4-dioxo-7-aryl-2,3,4,4a,7,7a,8,9,10,11-decahydro-1H-pyrido[3,4-i] quinazoline-6-carbonitrile and 5-amino-2,4-dioxo-7-aryl-1,2,3,4,4a,7,7a,8,10,11-decahydrothiopyrano[3,4-i]quinazo-line-6-carbonitrile derivatives. This method has advantages of high yields, simple procedure and easy work-up.

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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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The simple synthesis of quinazoline-2,4-dione derivatives using Boc strategy

Cited by 10 publications

References 13 publications

DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate

DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate

Preparation of skeletally diverse quinazoline-2,4(1H,3H)-diones using Na₂SiO₃/SnFe₂O₄ catalytic system through a four-component reaction

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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The simple synthesis of quinazoline-2,4-dione derivatives using Boc strategy

Cited by 10 publications

References 13 publications

DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate

DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate

Preparation of skeletally diverse quinazoline-2,4(1H,3H)-diones using Na2SiO3/SnFe2O4 catalytic system through a four-component reaction

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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Preparation of skeletally diverse quinazoline-2,4(1H,3H)-diones using Na₂SiO₃/SnFe₂O₄ catalytic system through a four-component reaction