A Microwave-Assisted and Heteropolyacids-Catalysed Cyclocondensation Reaction for the Synthesis of 4(3H)-Quinazolinones

Ighilahriz, Karima; Boutemeur, Baya; Chami, Fariza; Rabia, C.; Hamdi, Maâmar; Hamdi, Safouane

doi:10.3390/molecules13040779

Cited by 42 publications

(18 citation statements)

References 28 publications

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“…NMR spectra of aminoquinazolinones (presented in figure 6) in CDCl 3 showed a singlet of 3 protons of methyl group at 2.6 , singlet of 2 protons of primary amino group at 4.8 and an aromatic multiplet in the region between 7.1 -8.1 . Moreover, structure of quinazolinone elucidated by NMR spectroscopy evidents that quinazolinone is a linear molecule because of 13 C signal corresponding to the carbonyl carbon, C4, exists as a doublet with J CH = 3.0 Hz. This is indicative of coupling through 3 bonds, a condition that is met by the 4(3H)-quinazolinone but not with an angular 4-(1H)-quinazolinone [12].…”

Section: Nmr Spectroscopymentioning

confidence: 99%

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Quinazolinone Analogs as Potential Therapeutic Agents

Sharma¹,

Kaur²,

Pahwa

et al. 2011

CMC

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Quinazolinone scaffold has been considered as a magic moiety possessing myriad spectrum of medicinal activities. Diversity of biological response profile has attracted considerable interest of several researchers across the globe to explore this skeleton for its assorted therapeutic significance. Various novel classes of structurally different quinazolinones have been designed and synthesized depicting potential interventions such as antibacterial, antifungal, antiviral, anticonvulsant, CNS depressant, antiinflammatory, antihistaminic, anticancer and so on. Moreover, the nucleus constitutes an integral structural component in a number of drugs currently employed in several clinical therapies. The present paper is an earnest attempt to provide an insight view on the current medicinal aspects of quinazolinone heterocycles alongwith brief discussion of their chemistry.

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Section: Nmr Spectroscopymentioning

confidence: 99%

“…Both 1 H and 13 C NMR have been employed as important tools to confirm the structures of the derivatives as well as regioselective isomers. Gursoy et al evaluated the 1 H-NMR spectra in DMSO-d 6 and revealed the existence of two isomers.…”

Section: Nmr Spectroscopymentioning

confidence: 99%

Quinazolinone Analogs as Potential Therapeutic Agents

Sharma¹,

Kaur²,

Pahwa

et al. 2011

CMC

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“…For the preparation of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolinones in drug discovery efforts, Liu and co-workers [120] investigated a simple process for access of the quinazoline moiety from commercially available methyl and substituted iso(thio)cyanates. Under microwave irradiation, the short reaction time (20 min) and mild reaction conditions ( O) coupled to microwave irradiation allowed a solventless, rapid (13 min) and high-yielding preparation of 4(3H)-quinazolinones by condensation of anthranilic acid, aniline, and an orthoester (or formic acid) [121]. A series of novel 2,4-disubstituted quinazoline-based chemical entities as potent Pin1 inhibitors with IC 50 values at the micromolar level were synthesized in high yield from anthranilic acids and urea under microwave irradiation [122].…”

Section: Synthesis Of Quinazolines and Related Compoundsmentioning

confidence: 99%

Microwaves in Heterocyclic Chemistry

Bazureau

Paquin

Carrié

et al. 2012

Microwaves in Organic Synthesis

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“…A series of methods has been developed previously for the synthesis of 3-substituted 4(3H)-quinazolinones from anthranilic acid, orthoesters, and amines in the presence of various catalysts [1][2][3][4][5][6][7][8]. The drawbacks of these methods are expensive catalyst, high temperature (60-80 o C), long reaction time (20 h), etc.…”

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Synthesis of 3-substituted 4(3h)-quinazolinones catalyzed by ceric ammonium nitrate

Wang

Song

Zhang

2010

Chem Heterocycl Comp

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The synthesis of 3-substituted 4(3H)-quinazolinones from anthranilic acid, orthoesters, and amines in the presence of ceric ammonium nitrate has been studied. The reaction occurred in a few minutes at room temperature under solvent-free conditions and in excellent yields. The probable conversion mechanism has been discussed.One of the most frequently encountered heterocyclic compounds in medicinal chemistry is 4(3H)-quinazolinone, which exhibits interesting pharmacological activities. A series of methods has been developed previously for the synthesis of 3-substituted 4(3H)-quinazolinones from anthranilic acid, orthoesters, and amines in the presence of various catalysts [1][2][3][4][5][6][7][8]. The drawbacks of these methods are expensive catalyst, high temperature (60-80 o C), long reaction time (20 h), etc. In addition, anilines having strong electron-withdrawing substituents, e.g., Cl and NO 2 , gave generally no products at room temperature in previous reports. Hence, it was of interest to develop a more universal method for the synthesis of these products.During the course of our studies towards the development of green catalytic processes, we found that ceric ammonium nitrate (CAN) as an inexpensive and commercially available catalyst can efficiently catalyze one-pot synthesis of 3-substituted 4(3H)-quinazolinones 4 via triple-component condensation of anthranilic acid 1, orthoesters 2, and amines 3 (Scheme 1). The reaction was carried out under solvent-free conditions at room temperature. The triple-component interaction has been studied in the present work with the aim of extending the scope of reactants and of clarifying the mechanism.First, a blank experiment with anthranilic acid, triethyl orthoformate, and aniline in the absence of a catalyst was investigated. The result showed that only 5% product was obtained after 1 h. Then the scope and limitations of the condensation of anthranilic acid 1, triethyl or trimethyl orthoformate 2, and different substituted arylamines or alkylamine 3 catalyzed by CAN were studied; the results are shown in Table 1. All the reactions proceeded smoothly at room temperature. Both triethyl orthoformate and trimethyl orthoformate

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A Microwave-Assisted and Heteropolyacids-Catalysed Cyclocondensation Reaction for the Synthesis of 4(3H)-Quinazolinones

Cited by 42 publications

References 28 publications

Quinazolinone Analogs as Potential Therapeutic Agents

Quinazolinone Analogs as Potential Therapeutic Agents

Microwaves in Heterocyclic Chemistry

Synthesis of 3-substituted 4(3h)-quinazolinones catalyzed by ceric ammonium nitrate

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