Indium(III) Chloride: An Efficient Catalyst for One-Pot Multicomponent Synthesis of 2,3-dihydroquinazoline-4(1H)-ones

Sahu, Adarsh; Mishra, Subhajit; Sahu, Preeti; Gajbhiye, Asmita; Agrawal, Ram Kishore

doi:10.2174/2213337205666180614112318

Cited by 16 publications

(11 citation statements)

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“…To carry out the molecular docking, the AutoDock Vina suite [44][45][46] was used, which is available in YASARA [38][39][40][41][42] using dock run macro. The cube box type with a size of 20 Å bigger than the active site of the protein is used for making the simulation cell.…”

Section: Molecular Dockingmentioning

confidence: 99%

Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

et al. 2023

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Quinoline-based compounds are one of the most important classes of N-heterocyclics exhibiting a wide spectrum of biological activities. There is a constant demand for the synthesis of new quinoline-based molecules suitable for therapeutic applications. Here a new strategy is developed to synthesize different quinoline-based quinazolinones catalytically using InCl 3 through a cyclocondensation reaction of isatoic anhydride and aniline with 2-substituted-quinoline-3-carbaldehyde to produce 2-(2-phenoxyquinolin-3-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives (> 90 % yields). In contrast, the reduced electrophilicity at the metal center allows the hydrazide ligand to bind In(III) and serendipitously forms benzoic(2-phenoxyquinoline-3-carbonyl) carbamic anhydride (∼ 70 % yields). The mechanistic aspects of these reactions were rationally explained. The structure and purity of all the isolated derivatives were assessed by spectroscopic and analytical data. In view of a strong correlation existing between inflammation and cancer progression, the ex-vivo anti-inflammatory effect of the ligands was established. The anti-cancer property of the proposed ligand was delineated with a specific SIRT protein family. Further, the computational docking studies on the binding abilities of 22 synthesized compounds with the Sirt1 protein were discussed in detail.

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Section: Molecular Dockingmentioning

confidence: 99%

Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

et al. 2023

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“…In 2018, Sahu and co-workers observed InCl 3 catalyzed condensation of isatoic anhydride 43, aromatic aldehydes 44 and ammonium chloride in ethanol under reflux condition furnished 2,3-dihydroquinazoline-4(1H)-ones 45 in a yield between 84-95 %. [44] In this one-pot multicomponent reaction ethanol act as a green solvent and ammonium chloride supply nitrogen atom to form the nitrogen containing heterocycles. The results are summarized in Scheme 12 using various aldehydes.…”

Section: Mrityunjoymentioning

confidence: 99%

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Datta

2021

ChemistrySelect

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This review summarizes recent advances of indium trichloride catalyzed synthesis of different organic compounds. It is obvious that InCl3 co‐ordinates with C−C and/or C‐heteroatom multiple bonds and thereby makes them very prone to nucleophilic attack to form a new bond. This Lewis acid catalyst also activates oxiranes to produce aldehydes. Multicomponent synthesis including C−C bond formation reaction and construction of N, O and S‐containing heterocycles are discussed in organic solvents as well as in water. This article highlights recent developments and application of indium(III) chloride as a catalyst in organic synthesis from 2015 to 2020. The mechanism of few important reactions is discussed in detail which will be very useful for the readers.

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“…The generated library (10 examples) was prepared in excellent yields and in slightly shorter reaction times. [53] Scheme 18. InCl 3 -catalyzed 2,3-dihydroquinazolin-4(1H)-one synthesis.…”

Section: Miscellaneousmentioning

confidence: 99%

“…As a matter of fact, the already described reaction to obtain 2,3‐dihydroquinazolin‐4(1 H )‐ones using indium oxide NPs (Scheme C ) was recently explored by Sahu et al ., using indium(III) as the catalyst (Scheme ). The generated library (10 examples) was prepared in excellent yields and in slightly shorter reaction times …”

Section: Miscellaneousmentioning

confidence: 99%

A Decade of Indium‐Catalyzed Multicomponent Reactions (MCRs)

2020

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In the context of synthetic chemistry, Indium is one of the least explored elements of the notorious group 13 of the periodic table and has not attracted quite the same amount of attention as its fellow members, Aluminium and Boron, which have shown unprecedented synthetic applications for more than half a century. Nonetheless, Indium has emerged in recent years as a very valuable catalyst for multicomponent reactions. From the use of indium powder or easily accessible and cheap indium salts to more complex indium‐based metal‐organic frameworks or nanoparticles, a plethora of applications has been described throughout this last decade, showcasing not only the versatility of indium catalysis but also how much there is still to be explored. In the aftermath of the international year of the periodic table of the chemical elements in 2019, we navigated through the large inventory of multicomponent reactions (MCRs) to encounter the types of useful reactions leading to important target compounds (many of which are biologically active) catalyzed by this d‐block post‐transition metal.

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Indium(III) Chloride: An Efficient Catalyst for One-Pot Multicomponent Synthesis of 2,3-dihydroquinazoline-4(1H)-ones

Cited by 16 publications

References 0 publications

Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

A Decade of Indium‐Catalyzed Multicomponent Reactions (MCRs)

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