Pseudo-five-component organocatalyzed synthesis of dicyanoanillines using only malononitrile and aromatic aldehydes

Background: In this study, we developed a convenient methodology for the synthesis of coumarin linked to pyrazolines and pyrano [2,3-h] coumarins linked to 3-(1,5-diphenyl-4,5- dihydro-1H-pyrazol-3-yl)-chromen-2-one derivatives using Chlorosulfonic acid supported Piperidine-4-carboxylic acid (PPCA) functionalized Fe3O4 nanoparticles (Fe3O4-PPCA) catalyst. Materials and Methods:: Fe3O4-PPCA was investigated as an efficient and magnetically recoverable Nanocatalyst for the one-pot synthesis of substituted coumarins from the reaction of coumarin with a variety of aromatic aldehydes in high to excellent yield at room temperature under solvent-free conditions. The magnetic nanocatalyst can be easily recovered by applying an external magnet device and reused for at least 10 reaction runs without considerable loss of reactivity. Results and Conclusion: The advantages of this protocol are the use of commercially available materials, simple and an inexpensive procedure, easy separation, and an eco-friendly procedure, and it shows good reaction times, good to high yields, inexpensive and practicability procedure, and high efficiency.

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Microwave assisted synthesis of novel Pyrazole derivatives and their biological evaluation as anti-bacterial agents

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/1386207323666201019152206 ◽

2020 ◽

Vol 23 ◽

Author(s):

Hadis Khodadad ◽

Farhad Hatamjafari ◽

Khalil Pourshamsian ◽

Babak Sadeghi

Keyword(s):

Antibacterial Activity ◽

Aromatic Aldehydes ◽

Catalytic Amount ◽

Antibacterial Activities ◽

Structural Features ◽

Biological Evaluation ◽

Aureus Strain ◽

Microwave Assisted Synthesis ◽

Pyrazole Derivatives ◽

Microwave Assisted

Aim and Objective: Microwave-assisted condensation of acetophenone 1 and aromatic aldehydes 2 gave chalcone analogs 3, which were cyclized to pyrazole derivatives 6a-f via the reaction with hydrazine hydrate and oxalic acid in the presence of the catalytic amount of acetic acid in ethanol. Materials and Methods: The structural features of the synthesized compounds were characterized by melting point, FT-IR, 1H, 13C NMR and elemental analysis. Results: The antibacterial activities of the synthesized pyrazoles was evaluated against three gram-positive bacteria such as Enterococcus durans, Staphylococcus aureus, Bacillus subtilis and two gram-negative bacteria such as Escherichia coli and Salmonella typhimurium. Conclusion: All the synthesized pyrazoles showed relatively high antibacterial activity against S. aureus strain and none of them demonstrated antibacterial activity against E. coli.

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Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/1386207321666180416153112 ◽

2018 ◽

Vol 21 (4) ◽

pp. 298-301 ◽

Cited By ~ 3

Author(s):

Ghasem Marandi

Keyword(s):

Biological Sciences ◽

Carboxylic Acid ◽

Carboxylic Acids ◽

High Performance ◽

Condensation Reaction ◽

Aromatic Aldehydes ◽

New Materials ◽

One Pot ◽

High Yields ◽

Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

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Synthesis and Kinetics of Highly Substituted Piperidines in the Presence of Tartaric Acid as a Catalyst

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/1386207321666180228115130 ◽

2018 ◽

Vol 21 (4) ◽

pp. 302-311

Author(s):

Younes Ghalandarzehi ◽

Mehdi Shahraki ◽

Sayyed M. Habibi-Khorassani

Keyword(s):

Ambient Temperature ◽

Tartaric Acid ◽

Aromatic Aldehydes ◽

One Pot ◽

Rate Determining Step ◽

State Approximation ◽

Solvent Free Conditions ◽

Steady State Approximation ◽

Absorbance Changes ◽

The One

Aim & Scope: The synthesis of highly substituted piperidine from the one-pot reaction between aromatic aldehydes, anilines and β-ketoesters in the presence of tartaric acid as a catalyst has been investigated in both methanol and ethanol media at ambient temperature. Different conditions of temperature and solvent were employed for calculating the thermodynamic parameters and obtaining an experimental approach to the kinetics and mechanism. Experiments were carried out under different temperature and solvent conditions. Material and Methods: Products were characterized by comparison of physical data with authentic samples and spectroscopic data (IR and NMR). Rate constants are presented as an average of several kinetic runs (at least 6-10) and are reproducible within ± 3%. The overall rate of reaction is followed by monitoring the absorbance changes of the products versus time on a Varian (Model Cary Bio- 300) UV-vis spectrophotometer with a 10 mm light-path cell. Results: The best result was achieved in the presence of 0.075 g (0.1 M) of catalyst and 5 mL methanol at ambient temperature. When the reaction was carried out under solvent-free conditions, the product was obtained in a moderate yield (25%). Methanol was optimized as a desirable solvent in the synthesis of piperidine, nevertheless, ethanol in a kinetic investigation had none effect on the enhancement of the reaction rate than methanol. Based on the spectral data, the overall order of the reaction followed the second order kinetics. The results showed that the first step of the reaction mechanism is a rate determining step. Conclusion: The use of tartaric acid has many advantages such as mild reaction conditions, simple and readily available precursors and inexpensive catalyst. The proposed mechanism was confirmed by experimental results and a steady state approximation.

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1, 1’-Sulfinyldiethylammonium Bis (Hydrogen Sulfate) as a Recyclable Dicationic Ionic Liquid Catalyst for the Efficient Solvent-free Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/1386207323666200127113743 ◽

2020 ◽

Vol 23 (2) ◽

pp. 157-167

Author(s):

Zainab Ehsani-Nasab ◽

Ali Ezabadi

Keyword(s):

Ionic Liquid ◽

Biginelli Reaction ◽

Aromatic Aldehydes ◽

Solvent Free ◽

Hydrogen Sulfate ◽

One Pot ◽

Acidic Ionic Liquid ◽

Brønsted Acidic Ionic Liquid ◽

Solvent Free Conditions ◽

Dicationic Ionic Liquid

Objective: A facile and efficient method for synthesis of 3, 4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by a novel dicationic Brönsted acidic ionic liquid, [(EtNH2)2SO][HSO4]2, has been successfully developed. Material and Method:: 3, 4-Dihydropyrimidin-2(1H)-ones were synthesized through one-pot condensation of aromatic aldehydes, ethyl acetoacetate, and urea under solvent-free conditions using [(EtNH2)2SO][HSO4]2 as a novel catalyst. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate / n-hexane = 1 / 5). The products have been characterized by IR, 1H NMR, 13C NMR, and also by their melting points. Results: In this research, a library of dihydropyrimidinone derivatives was synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as a catalyst. Various aromatic aldehydes, as well as heteroaromatic aldehydes, were employed, affording good to high yields of the corresponding products and illustrating the substrate generality of the present method. In addition, the prepared dicationic Brönsted acidic ionic liquid can be easily recovered and reused. Conclusion: 1, 1’-Sulfinyldiethylammonium bis (hydrogen sulfate), as a novel dicationic ionic liquid, can act as a highly efficient catalyst for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions.

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Synthesis, Characterization, Anti-proliferative Evaluation, and DNA Flow Cytometry Analysis of Some 2-Thiohydantoin Derivatives

Mini-Reviews in Medicinal Chemistry ◽

10.2174/1389557520666200611093510 ◽

2020 ◽

Vol 20 (18) ◽

pp. 1929-1941

Author(s):

Heba A. Elhady ◽

Hossa F. Al-Shareef

Keyword(s):

Anticancer Activity ◽

Schiff Bases ◽

Anticancer Agents ◽

Proliferative Activity ◽

Cancer Cell Line ◽

Aromatic Aldehydes ◽

Pharmaceutical Chemistry ◽

Dna Flow Cytometry ◽

Quinazoline Derivative ◽

Reference Drug

Background and Objective: Due to the well-documented anti-proliferative activity of 2-thiohydantoin incorporated with pyrazole, oxadiazole, quinazoline, urea, β-naphthyl carbamate and Schiff bases, they are noteworthy in pharmaceutical chemistry. Methods: An efficient approach for the synthesis of a novel series of 2-thiohydantoin derivatives incorporated with pyrazole and oxadiazole has proceeded via the reaction of the acyl hydrazide with chalcones and/or triethyl orthoformate. Schiff bases were synthesized by the reaction of the acyl hydrazide with different aromatic aldehydes. Moreover, Curtius rearrangement was applied to the acyl azide to obtain the urea derivative, quinazoline derivative, and carbamate derivative. Results: The synthesized compounds structures were discussed and confirmed depending on their spectral data. The anticancer activity of these heterocyclic compounds was evaluated against the breast cancer cell line (MCF-7), where they showed variable activity. Compound 5d found to have a superior anticancer activity, where it has (IC50 = 2.07 ± 0.13 μg/mL) in comparison with the reference drug doxorubicin that has (IC50 = 2.79 ± 0.07 μg / mL). Then compound 5d subjected to further studies such as cell cycle analysis and apoptosis. Apoptosis was confirmed by the upregulation of Bax, downregulation of Bcl-2, and the increase of the caspase 3/7percentage. Conclusion: Insertion of pyrazole, oxadiazole and, quinazoline moieties with 2-thiohydantoin moiety led to the enhancement of its anti-proliferative activity. Hence they can be used as anticancer agents.

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Zinc Sulfamate Catalyzed Efficient Selective Synthesis of Benzimidazole Derivatives under Ambient Conditions

Letters in Organic Chemistry ◽

10.2174/1570178616666181211094040 ◽

2019 ◽

Vol 16 (9) ◽

pp. 740-749

Author(s):

Sushil R. Mathapati ◽

Arvind H. Jadhav ◽

Mantosh B. Swami ◽

Jairaj K. Dawle

Keyword(s):

Benzimidazole Derivative ◽

Sulfamic Acid ◽

Aromatic Aldehydes ◽

Catalytic Amount ◽

Product Yield ◽

Lewis Acidity ◽

Benzimidazole Derivatives ◽

Ambient Conditions ◽

Reaction Condition ◽

Green Approach

Zinc sulfamate (Zn(NH2SO3)2 is a derivative of sulfamic acid (H3NSO3) which possesses “Lewis acidity” and finds well suited in a number of catalytic applications. The present paper describes an efficient, eco-friendly, and clean synthesis of 2-substituted benzimidazole derivatives by reacting diverse o-phenylenediamine with various substituted aromatic aldehydes using a catalytic amount of zinc sulfamate in ethanol at ambient temperature. As a result, 10 mol.% of Zinc sulfamate catalyst showed 92% of respective product yield with 100% conversion using short reaction period in ethanol. Meanwhile, effect of reaction parameters, such as amount of catalyst, different solvents, and reaction temperature on reaction product, was also studied. In addition, in the optimized reaction condition various substituted biological important benzimidazoles derivatives were prepared by using optimized reaction condition in good to efficient yield. In addition, possible reaction mechanism in the presence of zinc sulfamate for the preparation of benzimidazole derivative was sketched and discussed. The present green approach showed significances with faster reaction rate with inexpensive catalyst, which showed excellent and clean yield of benzimidazole in mild reaction condition with easy work-up procedure.

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Visible Light Assisted Hantzsch Reaction: Synthesis of Polycyclic Dihydropyridines

Letters in Organic Chemistry ◽

10.2174/1570178615666181107095151 ◽

2019 ◽

Vol 16 (8) ◽

pp. 676-682

Author(s):

Ankusab Noorahmadsab Nadaf ◽

Kalegowda Shivashankar

Keyword(s):

Reaction Time ◽

Light Intensity ◽

Ammonium Acetate ◽

Low Cost ◽

Aromatic Aldehydes ◽

Light Irradiation ◽

High Yield ◽

Short Reaction Time ◽

Green Protocol ◽

Dihydropyridine Derivatives

The polycyclic dihydropyridine nucleus represents the heterocyclic system of invaluable core motifs with wide applications in chemical, biological and physical properties. Although this kind of compounds have been extensively synthesized by other groups, the synthesis of these compounds under CFL light intensity were not explored. The synthesis of polycyclic dihydropyridine derivatives were achieved through the reaction of 4-hydroxycoumarin, aromatic aldehydes and ammonium acetate under CFL light irradiation conditions. A series of polycyclic dihydropyridine derivatives were prepared under CFL light irradiation conditions with high yield, short reaction time, ambient condition and without the use of catalyst. The results displayed an efficient method for the synthesis of polycyclic dihydropyridine derivatives. Clean profile, short reaction time, low cost and use of CFL light intensity instead of catalyst making it a genuinely green protocol.

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Synthesis, Antiproliferative Activity and Molecular Docking of New Thiazole/Benzothiazole Fused Pyranopyrimidine Derivatives

Letters in Organic Chemistry ◽

10.2174/1570178617666200319114611 ◽

2020 ◽

Vol 17 (12) ◽

pp. 951-958

Author(s):

Pallava Nagaraju ◽

Pedavenkatagari Narayana Reddy ◽

Pannala Padmaja ◽

Vinod G. Ugale

Keyword(s):

Molecular Docking ◽

Cell Lines ◽

Antiproliferative Activity ◽

Aromatic Aldehydes ◽

Human Colon ◽

Docking Studies ◽

Human Colon Cancer ◽

One Pot ◽

Human Embryonic Kidney Cells ◽

Heterocyclic Molecules

A new class of 4H,5H-benzo[4,5]thiazolo[3,2-a]pyrano[2,3-d]pyrimidin-5-one and 5H,6Hpyrano[ 2,3-d]thiazolo[3,2-a]pyrimidin-5-one derivatives were synthesized via the one-pot threecomponent reaction of 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one and 7-hydroxy-5Hthiazolo[ 3,2-a]pyrimidin-5-one to various aromatic aldehydes and malononitrile. This domino transformation involves the formation of pyranopyrimidine ring by the formation of three C–C bonds and one C– O bond a single synthetic operation. As the products precipitate out of the reaction, simple filtration is enough to gather the products, and thus, there is no need for work-up or column-chromatography. The synthesized thiazole/benzothiazole fused pyranopyrimidine derivatives were evaluated for their antiproliferative activity against four cancer cell lines namely DU 145 (prostate cancer), Hela (Human cervical cancer), MDA-MB-231 (breast cancer), HT-29 (Human colon cancer) and normal cell line HEK293 (human embryonic kidney cells). The results demonstrated that synthesized compounds were selective in its cytotoxicity to cancer cells compared to normal cells. Among these compounds, 2-amino-9- methoxy-5-oxo-4-(3,4,5-trimethoxyphenyl)-4H,5H-benzo[4,5]thiazolo[3,2-a]pyrano[2,3-d]pyrimidine- 3-carbonitrile 4i exhibited the most potent antiproliferative activity against the tested cell lines. Molecular docking studies revealed that these active heterocyclic molecules bind selectively in the colchicine binding site of tubulin polymer.

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