scholarly journals Glutamic acid as green and bio-based α-amino acid catalyst promoted one-pot access to polyfunctionalized dihydro-2-oxypyrroles

2019 ◽  
Vol 84 (10) ◽  
pp. 1083-1092 ◽  
Author(s):  
Farzaneh Mohamadpour
Keyword(s):  
Amino Acid ◽  
Glutamic Acid ◽  
Acid Catalyst ◽  
Biologically Active ◽  
Domino Reaction ◽  
Solid Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Active Amino Acid ◽  
Work Up

A highly versatile and convenient synthetic route for biologically active ?-amino acid, glutamic acid catalyzed facile and mild preparation of polyfunctionalized dihydro-2-oxypyrroles via one-pot, four condensation domino reaction between aromatic/aliphatic amines, dialkyl acetylenedicarboxylates and formaldehyde have been studied. The route includes green, biodegradable and inexpensive ?-amino acid catalyst, high atom-economy, simplicity of operation and work-up procedures, without chromatographic purification steps. The solid catalyst, non-toxic or hazardous, easily handled with mild reaction conditions and excellent yields are the notable benefits of the highly efficient and expedient synthesis of these products.

Microwave Domino Diastereoselective Synthesis of Novel Trans-4,5-Dihydro-1H-Furo[2,3-c]Pyrazoles Using Pyridinium Salts in an Aqueous Medium

2018 ◽  
Vol 42 (4) ◽  
pp. 219-223 ◽  
Author(s):  
Afshin Yazdani-Elah-Abadi ◽  
Reza Morekian ◽  
Nasim Simin ◽  
Mojtaba Lashkari
Keyword(s):  
Hydrazine Hydrate ◽  
Pyridinium Salt ◽  
Biologically Active ◽  
Domino Reaction ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
One Pot ◽  
Aryl Aldehyde ◽  
High Yields ◽  
Work Up

Novel fused 4,5-dihydro-1 H-furo[2,3- c]pyrazole derivatives containing both biologically active pyrazole and furan templates are synthesised by a one-pot two-step four-component domino reaction involving hydrazine hydrate, a β-keto ester, an aromatic aldehyde and a pyridinium salt catalysed by DABCO with high diastereoselectivity in H2O under microwave irradiation. To minimise the formation of byproducts, the hydrazine hydrate and ethyl acetoacetate were first irradiated until a pyrazolone was formed. Next, the aryl aldehyde, the pyridinium salt and DABCO were added and the reaction could be completed in good to excellent yields. The salient features of this eco-friendly methodology are highlighted by its short reaction time (10–12 min), high yields, high atom-economy, efficiency of producing five new bonds (2C–C, C=N, C–N and one C–O), two new rings and two stereocentres in a single operation, absence of any tedious work-up or purification and avoidance of separation of intermediates.

Synthesis of pyrazolo[1,5-c]quinazoline derivatives through the copper-catalyzed domino reaction of o-alkenyl aromatic isocyanides with diazo compounds

2020 ◽  
Vol 56 (55) ◽  
pp. 7665-7668 ◽  
Author(s):  
Lu Liu ◽  
Lei Li ◽  
Shukuan Mao ◽  
Xin Wang ◽  
Ming-Dong Zhou ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Domino Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Quinazoline Derivatives

Various o-alkenyl aromatic isocyanides were prepared from readily available reactants for their double annulation with diazo compounds for a one-pot synthesis of pyrazolo[1,5-c]quinazolines under mild reaction conditions.

scholarly journals Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

2018 ◽  
Vol 14 ◽  
pp. 1655-1659 ◽  
Author(s):  
Ugo Azzena ◽  
Massimo Carraro ◽  
Gloria Modugno ◽  
Luisa Pisano ◽  
Luigi Urtis
Keyword(s):  
Organic Chemistry ◽  
Heterogeneous Catalysis ◽  
Important Class ◽  
Green Solvents ◽  
Reaction Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Acidic Catalysts ◽  
Set Up ◽  
Work Up

The application of heterogeneous catalysis and green solvents to the set up of widely employed reactions is a challenge in contemporary organic chemistry. We applied such an approach to the synthesis and further conversion of tetrahydropyranyl ethers, an important class of compounds widely employed in multistep syntheses. Several alcohols and phenols were almost quantitatively converted into the corresponding tetrahydropyranyl ethers in cyclopentyl methyl ether or 2-methyltetrahydrofuran employing NH4HSO4 supported on SiO2 as a recyclable acidic catalyst. Easy work up of the reaction mixtures and the versatility of the solvents allowed further conversion of the reaction products under one-pot reaction conditions.

An efficient multicomponent, one-pot synthesis of Betti bases catalyzed by cerium (IV) ammonium nitrate (CAN) at ambient temperature

2016 ◽  
Vol 5 (4) ◽  
Author(s):  
Ramadan Ahmed Mekheimer ◽  
Abdullah Mohamed Asiri ◽  
Afaf Mohamed Abdel Hameed ◽  
Reham R. Awed ◽  
Kamal Usef Sadek
Keyword(s):  
Ambient Temperature ◽  
Environmental Pollution ◽  
Ammonium Nitrate ◽  
Room Temperature ◽  
Catalytic Amount ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Work Up ◽  
Cerium Iv Ammonium Nitrate

AbstractStarting from readily available 2-naphthol, aldehydes, aryl and alkylamines, a variety of Betti bases were efficiently synthesized utilizing a catalytic amount of cerium (IV) ammonium nitrate (CAN) at room temperature. This protocol has advantages of high yield, mild reaction conditions, no environmental pollution, diversity of reactants and simple work up procedure.

scholarly journals Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

2013 ◽  
Vol 9 ◽  
pp. 2344-2353 ◽  
Author(s):  
Sudipta Pathak ◽  
Kamalesh Debnath ◽  
Animesh Pramanik
Keyword(s):  
Sulfuric Acid ◽  
Low Cost ◽  
Solvent Free ◽  
Primary Amines ◽  
Solid Catalyst ◽  
Silica Sulfuric Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Solvent Free Reaction

A convenient and efficient methodology for the synthesis of densely substituted pyrrole-fused isocoumarins, which employs solid-supported silica sulfuric acid (SSA) as catalyst, has been developed. When the mixture of ninhydrin adducts of acetylacetone/ethyl acetoacetate and primary amines was heated on the solid surface of SSA under solvent-free conditions, the pyrrole-fused isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the starting materials, and the excellent yields of products.

scholarly journals Microwave Assisted One Pot Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives using [Emim]OH Ionic Liquid as Novel Catalyst

2019 ◽  
Vol 31 (4) ◽  
pp. 829-833
Author(s):  
D.S. Bhagat ◽  
S.G. Pande ◽  
M.V. Katariya ◽  
R.P. Pawar ◽  
P.S. Kendrekar
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
Aryl Aldehydes ◽  
Microwave Assisted ◽  
Novel Catalyst ◽  
Work Up

One-pot efficient protocol to the synthesis of 2-amino-5-oxo-4,5-dihydropyrano(3,2-c)chromene-3-carbonitrile derivatives via condensation of various aryl aldehydes, dicyanomethane and 4-hydroxycoumarin in presence of Emim hydroxide as an excellent homogeneous liquid catalyst. The key advantages of this methodology are mild reaction conditions, novel catalyst, short reaction time, eco-friendly, easy work-up procedure and high yield of isolation of derivatives.

Lewis Acid Promoted, One-Pot Synthesis of Fluoroquinolone Clubbed 1,3,4-Thiadiazole Motifs under Microwave Irradiation: Their Biological Activities

2020 ◽  
Vol 7 (1) ◽  
pp. 60-66
Author(s):  
Navin B. Patel ◽  
Rahul B. Parmar ◽  
Hetal I. Soni
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Antitubercular Activity ◽  
Biologically Active ◽  
High Yield ◽  
One Pot ◽  
One Pot Synthesis ◽  
Lewis Acid Catalyst

Background: A Lewis acid promoted efficient and facile procedure for one-pot synthesis of a novel series of fluoroquinolone clubbed with thiadiazoles motifs under microwave irradiation is described here. This technique has more advantages such as high yield, a clean procedure, low reaction time, simple work-up and use of Lewis acid catalyst. Objective: Our aim is to generate a biologically active 1,3,4- thiadiazole ring system by using a onepot synthesis method and microwave-assisted heating. High yield and low reaction time were the main purposes to synthesize bioactive fluoroquinolone clubbed 1,3,4- thiadiazole moiety. Methods: Fluoroquinolone Clubbed 1,3,4-Thiadiazole Motifs was prepared by Lewis acid promoted, one-pot synthesis, under microwave irradiation. All the synthesized molecules were determined by IR, 1H NMR, 13C NMR, and Mass spectra. The antimicrobial activity of synthesized compounds was examined against two Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), two Gram-positive bacteria (Staphylococcus aureus, Streptococcus pyogenes), and three fungi (Candida albicans, Aspergillus niger, Aspergillus clavatus) using the MIC (Minimal Inhibitory Concentration) method and antitubercular activity H37Rv using L. J. Slope Method. Results: Lewis acid promoted, one-pot synthesis of Fluoroquinolone clubbed 1,3,4-Thiadiazole motifs under microwave irradiation is an extremely beneficial method because of its low reaction time and good yield. Some of these novel derivatives showed moderate to good in vitro antibacterial, antifungal, and antitubercular activity. Conclusion: One-pot synthesis of 1,3,4-Thiadiazole by using Lewis acid catalyst gives a good result for saving time and also getting more production of novel heterocyclic compounds with good antimicrobial properties via microwave heating method.

Synthesis of Fluorinated Aromatic Compounds by One-Pot Benzyne Generation and Nucleophilic Fluorination

2014 ◽  
Vol 67 (3) ◽  
pp. 475 ◽  
Author(s):  
Takashi Ikawa ◽  
Shigeaki Masuda ◽  
Tsuyoshi Nishiyama ◽  
Akira Takagi ◽  
Shuji Akai
Keyword(s):  
Aromatic Compounds ◽  
Biologically Active ◽  
Reaction Conditions ◽  
Fluoride Ions ◽  
One Pot ◽  
Substituted Benzenes ◽  
Fluorinated Aromatic Compounds ◽  
Nucleophilic Fluorination ◽  
Sequential Reactions

The fluorination of substituted benzenes using fluoride ions under mild reaction conditions has been one of the most important challenges for the synthesis of biologically active fluorinated aromatic compounds; however, only a few synthetically useful methods are known. In this paper, it is reported that the nucleophilic fluorination of benzynes, generated from either 2-(trialkylsilyl)phenyl nonafluorobutanesulfonates or 2-(trialkylsilyl)phenols, meets this challenge. In particular, the fluorination starting from 2-(trialkylsilyl)phenols for fabricating aryl fluorides involves three sequential reactions in one-pot: the nonaflylation of phenols, benzyne generation, and nucleophilic fluorination of the benzynes. The regioselectivities of these reactions are controlled by the substituents at the C3-position of the benzynes.

A Convenient One-Pot and Rapid Microwave-Assisted Synthesis of Biologically Active s-Triazolo[3,4-b][1,3,4]Thiadiazine and s-Triazolo[3,4-b][1,3,4]Thiadiazole Nanoarchitectonics

2020 ◽  
Vol 20 (5) ◽  
pp. 2917-2929
Author(s):  
Ahmed F. M. EL-Mahdy ◽  
Hassan A. H. EL-Sherief ◽  
Zeinab A. Hozien ◽  
Shiao-Wei Kuo
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Reaction Time ◽  
Catalytic Amount ◽  
Biologically Active ◽  
Microwave Assisted Synthesis ◽  
One Pot ◽  
Microwave Assisted ◽  
Work Up ◽  
Temperature Time

A rapid and efficient one-pot protocol has been developed for the synthesis of s-triazolo[3,4-b][1,3,4]thiadiazine and s-triazolo[3,4-b][1,3,4]thiadiazole nanoarchitectonics through the reaction of s-triazoles with ketones and nitriles in acetic acid containing a catalytic amount of sulfuric acid under microwave irradiation in excellent yields. With this catalytic reaction, the cheap sulfuric acid as well as other acids were examined as catalysts and the highly toxic and irritating haloketones and halonitriles were avoided to form. The effects of microwave power, temperature, time, solvent and catalyst were examined. This method achieved a better performance; e.g., higher yields, shorter reaction time and easier work-up as compared to other conventional methods. Therefore, the proposed method will be readily applicable to the synthesis of biologically important compounds containing s-triazolo[3,4-b][1,3,4]thiadiazine and s-triazolo[3,4-b][1,3,4]thiadiazole framework.

Stability Constants of Some Metal Complexes Formed by Mimosine and Related Compounds

1979 ◽  
Vol 32 (1) ◽  
pp. 21 ◽  
Author(s):  
H Stunzi ◽  
DD Perrin ◽  
T Teitei ◽  
RLN Harris
Keyword(s):  
Amino Acid ◽  
Stability Constants ◽  
Metal Binding ◽  
Acid Group ◽  
Biologically Active ◽  
Amino Acid Group ◽  
Dimeric Complexes ◽  
Major Species ◽  
Active Amino Acid ◽  
Related Compounds

Complex formation of the biologically active amino acid L-mimosine [α-amino-β-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid (1)], mimosinic acid (2), mimosine methyl ether (9) and 3-hydroxy-1-methylpyridin-4(1H)-one (4) with Cu2+, Zn2+, Cd2+ and Pb2+ was studied. Stability constants were determined by potentiometric titration in 0.15M KNOB3 as inert electrolyte at 37�. In the monomeric complexes formed by the mimosine derivatives, metal binding by the hydroxypyridone moiety was favoured relative to the amino acid group. With mimosine, dimeric complexes were major species. Under physiological conditions, mimosine binds copper and zinc ions more strongly than do simpler amino acids.

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