Introduction of a novel nanosized N-sulfonated Brönsted acidic catalyst for the promotion of the synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions

Omid Goli-Jolodar; Farhad Shirini; Mohadeseh Seddighi

doi:10.1039/c6ra04148e

Introduction of a novel nanosized N-sulfonated Brönsted acidic catalyst for the promotion of the synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions

RSC Advances ◽

10.1039/c6ra04148e ◽

2016 ◽

Vol 6 (31) ◽

pp. 26026-26037 ◽

Cited By ~ 41

Author(s):

Omid Goli-Jolodar ◽

Farhad Shirini ◽

Mohadeseh Seddighi

Keyword(s):

Sulfonic Acid ◽

Solvent Free ◽

Acidic Catalyst ◽

H Nmr ◽

Solvent Free Conditions ◽

Afm Analysis ◽

Hantzsch Condensation ◽

Different Types ◽

Ft Ir ◽

C Nmr

In this research NS-C4(DABCO-SO3H)2)·4Cl as a new nano sized N-sulfonic acid was prepared and characterized using different types of methods including FT-IR, 1H NMR, 13C NMR, mass, XRD, TGA, SEM and AFM analysis.

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Design, preparation and characterization of a new ionic liquid, 1,3-disulfonic acid benzimidazolium chloride, as an efficient and recyclable catalyst for the synthesis of tetrahydropyridine under solvent-free conditions

RSC Advances ◽

10.1039/c5ra10699k ◽

2015 ◽

Vol 5 (83) ◽

pp. 67405-67411 ◽

Cited By ~ 12

Author(s):

Mohsen Abbasi

Keyword(s):

Ionic Liquid ◽

Mass Spectra ◽

Recyclable Catalyst ◽

Solvent Free ◽

Disulfonic Acid ◽

H Nmr ◽

Solvent Free Conditions ◽

Ft Ir ◽

C Nmr

In the present work, 1,3-disulfonic acid benzimidazolium chloride as a new ionic liquid, is synthesized, and characterized by studying its FT-IR, 1H NMR, 13C NMR as well as mass spectra.

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Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Advances in Chemistry ◽

10.1155/2014/834641 ◽

2014 ◽

Vol 2014 ◽

pp. 1-4 ◽

Cited By ~ 1

Author(s):

Hamid Beyzaei ◽

Reza Aryan ◽

Zahra Keshtegar

Keyword(s):

Ring Opening ◽

Reaction Times ◽

Reaction Conditions ◽

Ir Spectrometry ◽

H Nmr ◽

Chemical Structures ◽

Thioamide Group ◽

Solvent Free Conditions ◽

Ft Ir ◽

C Nmr

Synthesis of new imidazolidine and tetrahydropyrimidine derivatives 3a, b and 4a–c as cyclic 1,3-diamines under two reaction conditions (A and B) is described. Under reaction conditions-A, a suspension of (E)-2-cyano-2-(oxazolidin-2-ylidene)ethanethioamide 1 (1 eq.) and diaminoalkanes 2a–e (2 eq.) in absolute ethanol is heated under reflux for 16–22 h to afford 3a, b and 4a–c. Alternatively, under reaction conditions-B, a solution of thioamide 1 (1 eq.) in diaminoalkanes 2a–e (3 eq.) is stirred under solvent-free conditions at room temperature for 3 days to give desired products. Reaction conditions-A for having higher yields, shorter reaction times, and required less diamines is more effective than reaction conditions-B. Oxazolidine ring opening is observed by reacting compound 1 with all of the diamines 2a–e, but the thioamide group only reacts with nonbulky diamines 2a, b. The chemical structures of novel compounds were confirmed by 1H NMR, 13C NMR, elemental analysis, and FT-IR spectrometry.

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ChemInform Abstract: Introduction of a Novel Nanosized N-Sulfonated Broensted Acidic Catalyst for the Promotion of the Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation under Solvent-Free Conditions.

ChemInform ◽

10.1002/chin.201630180 ◽

2016 ◽

Vol 47 (30) ◽

Author(s):

Omid Goli-Jolodar ◽

Farhad Shirini ◽

Mohadeseh Seddighi

Keyword(s):

Solvent Free ◽

Acidic Catalyst ◽

Solvent Free Conditions ◽

Hantzsch Condensation

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Synthesis and Nitration of 7-Hydroxy-4-Methyl Coumarin via Pechmann Condensation Using Eco-Friendly Medias

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.69.66 ◽

2016 ◽

Vol 69 ◽

pp. 66-73 ◽

Cited By ~ 7

Author(s):

Fadia Al Haj Hussien ◽

Mohammad Keshe ◽

Khaled Alzobar ◽

Joumaa Merza ◽

Ayman Karam

Keyword(s):

Biological Activity ◽

Coumarin Derivatives ◽

Melting Points ◽

Efficient Catalyst ◽

Amberlyst 15 ◽

H Nmr ◽

Pechmann Condensation ◽

Solvent Free Conditions ◽

Ft Ir ◽

C Nmr

A nitro coumarin derivatives has been synthesized via nitration of 7-hydroxy-4-methyl coumarin wich was synthesized via Pechmann condensation resorcinol with a β-ketoester using Amberlyst-15 as a green and efficient catalyst and by caring out the reaction of resorcinol and ethyl acetoacetate (with 1: 1 mol ratio) in the presence of 0.2 g of Amberlyst-15 at 110°C under solvent-free conditions. These nitro coumarin derivatives have biological activity and momentousness in the industrial fields. The purified products were measured the melting points and characterized by spectral methods: FT-IR,1H-NMR ,13C-NMR.

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Synthesis, Characterization, and Antioxidant Activity of Some 2-Methoxyphenols derivatives

Heterocyclic Communications ◽

10.1515/hc-2020-0112 ◽

2020 ◽

Vol 26 (1) ◽

pp. 112-122

Author(s):

Shaikha S. AlNeyadi ◽

Naheed Amer ◽

Tony G. Thomas ◽

Ruba Al Ajeil ◽

Priya Breitener ◽

...

Keyword(s):

Oxidative Stress ◽

Antioxidant Activity ◽

Sulfonic Acid ◽

Antioxidant Properties ◽

Causative Factor ◽

Oxygen Radical ◽

Design Synthesis ◽

H Nmr ◽

Ft Ir ◽

C Nmr

AbstractOxidative stress is a causative factor in the pathophysiology of numerous diseases, such as diabetes, atherosclerosis, cancer, and neurodegenerative and cardiovascular diseases. Therapeutic antioxidants are promising candidates for preventing and treating conditions in which oxidative stress is a contributing factor. In this study, we report the design, synthesis and antioxidant activity of six compounds containing the 2-methoxyphenol moiety core structure. The synthesized derivatives were characterized using 1H NMR, 13C NMR, Fourier-transform infrared (FT-IR), and elemental analysis spectroscopy. The antioxidant properties of the compounds were evaluated using the 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH), 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and oxygen radical absorbance capacity (ORAC) assay. New phenolic acid-derived compounds with antioxidant activity were identified.

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Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

SN Applied Sciences ◽

10.1007/s42452-021-04671-9 ◽

2021 ◽

Vol 3 (6) ◽

Author(s):

Kobra Nikoofar ◽

Fatemeh Shahriyari

Keyword(s):

Ionic Liquid ◽

Reaction Times ◽

Aromatic Aldehydes ◽

Environmentally Benign ◽

H Nmr ◽

Sonic Waves ◽

Ft Ir ◽

High Yields ◽

Work Up ◽

C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

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4-(Succinimido)-1-butane sulfonic acid as a Brönsted acid catalyst for synthesis of pyrano[4,3-b]pyran derivatives under solvent-free conditions

Chinese Chemical Letters ◽

10.1016/j.cclet.2014.10.009 ◽

2015 ◽

Vol 26 (1) ◽

pp. 26-30 ◽

Cited By ~ 22

Author(s):

Nader Ghaffari Khaligh

Keyword(s):

Sulfonic Acid ◽

Acid Catalyst ◽

Solvent Free ◽

Bronsted Acid ◽

Brønsted Acid ◽

Solvent Free Conditions ◽

Brönsted Acid ◽

Brønsted Acid Catalyst ◽

Brönsted Acid Catalyst

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SYNTHESIS AND STRUCTURAL ELUCIDATION OF AMINO ACETYLENIC AND THIOCARBAMATES DERIVATIVES FOR 2-MERCAPTOBENZOTHIAZOLE AS ANTIMICROBIAL AGENTS

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i2.15760 ◽

2017 ◽

Vol 9 (2) ◽

pp. 192

Author(s):

Aseel Alsarahni ◽

Zuhair Muhi Eldeen ◽

Elham Al-kaissi ◽

Ibrahim Al- Adham ◽

Najah Al-muhtaseb

Keyword(s):

Antimicrobial Activity ◽

Elemental Analysis ◽

Antimicrobial Agents ◽

Diffusion Method ◽

Benzothiazole Derivatives ◽

H Nmr ◽

Ft Ir ◽

Potential Antimicrobial Activity ◽

C Nmr

Objective: To design and synthesize amino acetylenic and thiocarbonate of 2-mercapto-1,3-benthiazoles as potential antimicrobial agents.Methods: A new series of 2-{[4-(t-amino-1-yl) but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole derivatives (AZ1-AZ6), and S-1,3-benzothiazol-2-yl-O-alkyl carbonothioate derivatives were synthesised, with the aim that the target compounds show new and potential antimicrobial activity. The elemental analysis was indicated by the EuroEA elemental analyzer, and biological characterization was via IR, 1H-NMR, [13]C-NMR, DSC were determined with the aid of Bruker FT-IR and Varian 300 MHz spectrometer using DMSO-d6 as a solvent. In vitro antimicrobial activity, evaluation was done for the synthesised compounds, by agar diffusion method and broth dilution test. The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were determined. Results: The IR, 1H-NMR, 13C-NMR, DSC and elemental analysis were consistent with the assigned structures. Compound of 2-{[4-(4-methylpiperazin-1-yl)but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole (AZ1), 2-{[4-(2-methylpiperidin-1-yl)but-2-yn-1-yl]sulfanyl}-1,3-benzothiazole (AZ2), 2-{[4-(piperidin-1-yl) but-2-yn-1-yl]sulfanyl}-1, 3-benzothiazole (AZ6), S-1,3-benzothiazol-2-yl-O-ethyl carbonothioate (AZ7), and S-1,3-benzothiazol-2-yl-O-(2-methylpropyl) carbonothioate (AZ9) showed the highest antimicrobial activity against Pseudomonas aeruginosa (P. aeruginosa), AZ-9 demonstrated the highest antifungal activity against Candida albicans (C. albicans), with MIC of 31.25 µg/ml.Conclusion: These promising results promoted our interest to investigate other structural analogues for their antimicrobial activity further.

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Synthesis of Novel Compounds as New Potent Tyrosinase Inhibitors

BioMed Research International ◽

10.1155/2013/207181 ◽

2013 ◽

Vol 2013 ◽

pp. 1-7 ◽

Cited By ~ 8

Author(s):

Hooshang Hamidian

Keyword(s):

Kojic Acid ◽

Azo Compounds ◽

The Novel ◽

Mushroom Tyrosinase ◽

Reference Standard ◽

Tyrosinase Inhibition ◽

H Nmr ◽

Ft Ir ◽

Tyrosinase Inhibitors ◽

C Nmr

In the present paper, we report the synthesis and pharmacological evaluation of a new series of azo compounds with different groups (1-naphthol, 2-naphthol, andN,N-dimethylaniline) and trifluoromethoxy and fluoro substituents in the scaffold. All synthesized compounds (5a–5f) showed the most potent mushroom tyrosinase inhibition (IC50values in the range of 4.39 ± 0.76–1.71 ± 0.49 µM), comparable to the kojic acid, as reference standard inhibitor. All the novel compounds were characterized by FT-IR,1H NMR,13C NMR, and elemental analysis.

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