InCl3-catalysed synthesis of 2-aryl quinazolin-4(3H)-ones and 5-aryl pyrazolo[4,3-d]pyrimidin-7(6H)-ones and their evaluation as potential anticancer agents

Mulakayala, Naveen; Kandagatla, Bhaskar; Ismail, Ismail; Rapolu, Rajesh Kumar; Rao, Praveen; Mulakayala, Chaitanya; Kumar, Chitta Suresh; Iqbal, Javed; Oruganti, Srinivas

doi:10.1016/j.bmcl.2012.06.003

Cited by 54 publications

(18 citation statements)

References 40 publications

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“…Numerous methods have been developed for the synthesis of pyrazolopyrimidinones from 4‐amino‐2‐methyl‐5‐propyl‐2 H ‐pyrazole‐3‐carboxylic acid amide including InCl 3 catalyzed synthesis by condensation with aldehydes, palladium catalyzed reaction with aryl halides (two examples), however, these are associated with limitations of use of metal catalyst, lower reaction yields and low substrate scope. Some reagents have also been used for the synthesis of pyrazolopyrimidinones from 4‐amino‐2‐methyl‐5‐propyl‐2 H ‐pyrazole‐3‐carboxylic acid amide by condensation with aldehydes, imines and carboxylic acids either using acid catalyst or iodine.…”

Section: Introductionmentioning

confidence: 99%

Transition Metal-free Single Step Approach for Arylated Pyrazolopyrimidinones and Quinazolinones Using Benzylamines/Benzylalcohols/Benzaldehydes

et al. 2017

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A transition metal-free, one step approach has been developed for the synthesis of pyrazolopyrimidinones using in-situ condensation of benzylamines, benzylalcohol and benzaldehyde with 4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid amide promoted by K 2 S 2 O 8 and water at room temperature. Present protocol tolerated various functional groups such as halides (Cl, F, Br), methoxy, ethoxy, hydroxyl, nitro, trifluromethyl, trifluoromethoxy and was also applicable to heterocyclic moieties. Different arylated pyrazolopyrimidinones were prepared in good to excellent yields. In the present reaction, K 2 S 2 O 8 is catalyzing the formation of imine as well helping in the cyclization to the desired product. We also reduced the industrially used synthesis steps for sildenafil analogues and prepared in three steps using present method. Arylquinazolinones were also synthesized in high yields using anthranilamide and benzylamines by this methodology.

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Section: Introductionmentioning

confidence: 99%

Transition Metal-free Single Step Approach for Arylated Pyrazolopyrimidinones and Quinazolinones Using Benzylamines/Benzylalcohols/Benzaldehydes

et al. 2017

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“…Quinazolinones and many substituted quinazolinone derivatives possess a wide range of biological activities , including anti tubercular, antibacterial, anticonvulsant, anticancer, and anti‐inflammatory . Also, structure activity relationship studies of quinazolinone derivatives have revealed that substitution at 4‐position of the quinazolinone ring can improve their antimicrobial and anticancer activities .…”

Section: Introductionmentioning

confidence: 99%

Survey Reactivity of Some Substituted Quinazolinones with Pentafluoro(chloro)pyridine

Ranjbar‐Karimi

Davodian

Mehrabi

2017

Journal of Heterocyclic Chem

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A new series of 4‐hetroaryl substituted quinazolines were designed and synthesized by the reaction of pentafluoro(chloro)pyridine and 2‐substituted quinazolinone. The aromatic nucleophilic substitution of pentafluoro(chloro)pyridine with quinazolinone occurs at the 4‐position of pyridine ring by the oxygen site (O‐centered nucleophile) of quinazolinone. The structures of all the compounds were confirmed by IR, 1H NMR, 19F NMR, and 13C NMR spectroscopy as well as elemental analysis.

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“…The prominent potencies associated with quinazoline containing compounds are their anticancer,anti-inflammatory, anthelmintic, analgesic, and anticonvulsive activities [1][2][3][4][5] .…”

Section: Introductionmentioning

confidence: 99%

An Efficient an One-Pot Method for Synthesis of 2-Aryl-(3H)-4-Quinazolinones Derivatives Catalyzed by SSA

Hatamjafari¹,

Eslami²

2014

Orient. J. Chem.

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A mixture of 2-amino benzamide with aromatic aldehyds in the presence of SSA under solvent-free condition were converted to quinazolinones with good yields.Key words: Starch SulphuricAcid (SSA), (3H)-4-Quinazolinones, One-pot, Solvent-Free . used in the synthesis of quinazolinone derivatives [6][7][8][9][10][11][12][13][14] .The early method, based on the reaction of 2-aminobenzamide with aldehyds, was performed in the presence of H 2 SO 4 and as a requirement of its refluxing condition much excess of aldehyds was used 15 .Though an excess of aldehyds is necessary to diminish the intermolecular side-reactions, the conventional beating method ever needs additional aldehyds both to improve the yield. In contrast to the Liquid H 2 SO 4, which is difficult to recovery and takes some effort in workup, the silica-supported H 2 SO 4, can be easily separated and recycled without the loss of activity for several times. Thus, 2-aminobenzamides (1) reacted with nearly 2 equivalents of aromatic aldehyds (2) 833-835 (2014) submission to microwave irradiation to provide fairly high yields of substituted quinazolin-4(3H)-ones (2a-d) in 25 minutes.However, these reactions often require harsh conditions and long reaction time and low efficiency can. Aromatic aldehydes, especially when used to replace for synthesis quinazolinones. Previously, we have synthesized a number of heterocyclic compounds [16][17][18][19][20][21][22][23][24][25][26][27][28] . Herein we report some of quinazolinones at one pot reaction, environmentally friendly with high yields and easy separation (Scheme 1). General Procedure for the Preparation of (3H)-4-Quinazolinone DerivativesA mixture of aldehyde (1 mmol) and2-amino benzamide (1 mmol), and starch sulphuric acid (20 W%) as a catalyst was stirred at 80 o C for 25 min. The progress of reaction was monitored by TLC. After finishing, recrystallized from ethanol 95% to give pure products (2a-d) 2-(3-nitrophenyl)-(3H)-4-Quinazolinone (2a)Pale 2-(4-methoxyphenyl)-(3H)-4-Quinazolinone (2b)Yellow crystals, Yield: %72, m.p= 245-248°C , FT-IR (V max /cm -1 ) (KBr disc): 3410 (amid NH Str.); 3131(arom. CH Str.); 2990(aliph. CH Str.); 1675(amid C=O Str.); 1643(C=N Str.). 2-(4-chlorophenyl)-(3H)-4-Quinazolinone (2c)White crystals, Yield: 89%, m.p = 302-304°C In conclusion, in comparison with the precedent related methods which show drawbacks from the standpoints of, prolong refluxing in solvent, need to inert gas, and consuming more aldehyds, the notable advantages of this methodology are: mild conditions in a solvent-free system, fairly high yields, fast reaction, no aqueous work-up and safe and environmental friendly conditions.

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InCl3-catalysed synthesis of 2-aryl quinazolin-4(3H)-ones and 5-aryl pyrazolo[4,3-d]pyrimidin-7(6H)-ones and their evaluation as potential anticancer agents

Cited by 54 publications

References 40 publications

Transition Metal-free Single Step Approach for Arylated Pyrazolopyrimidinones and Quinazolinones Using Benzylamines/Benzylalcohols/Benzaldehydes

Transition Metal-free Single Step Approach for Arylated Pyrazolopyrimidinones and Quinazolinones Using Benzylamines/Benzylalcohols/Benzaldehydes

Survey Reactivity of Some Substituted Quinazolinones with Pentafluoro(chloro)pyridine

An Efficient an One-Pot Method for Synthesis of 2-Aryl-(3H)-4-Quinazolinones Derivatives Catalyzed by SSA

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