A Three-Component Reaction for the One-Pot Preparation of β-Amino-α,α-Difluoroketones from Trimethyl(trifluoromethyl)silane (CF3TMS), Acylsilanes and Imines

Synthesis ◽  
2017 ◽  
Vol 49 (17) ◽  
pp. 4082-4092 ◽  
Author(s):  
Aurélien Honraedt ◽  
Lucía Méndez ◽  
Jean-Marc Campagne ◽  
Eric Leclerc
Keyword(s):  
Catalytic Amount ◽  
Fluoride Anion ◽  
One Pot ◽  
Three Component Reaction ◽  
Brook Rearrangement ◽  
Direct Preparation ◽  
Diphenylphosphinyl Imines ◽  
The One

A methodology allowing the direct preparation of β-amino-α,α-difluoroketones from the Ruppert–Prakash reagent (CF3TMS), acyltrimethylsilanes and N-Boc or N-(diphenylphosphinyl)imines is reported. The process, initiated by a catalytic amount of tetra-n-butylammonium difluorotriphenylsilicate (TBAT), involves the addition of CF3TMS to the acylsilane, followed by a Brook rearrangement and elimination of a fluoride anion. The latter promotes the addition of the resulting difluoroenoxysilane to the imine. The higher electrophilicity of the acylsilane compared to the imine allows the direct mixing of all the reagents in a three-component, one-pot process.

scholarly journals Phospho sulfonic acid: A novel and efficient solid acid catalyst for the one-pot preparation of 2H-indazolo[2,1-b]-phthalazine-triones

2013 ◽  
Vol 78 (4) ◽  
pp. 469-476 ◽  
Author(s):  
Reza Kiasat ◽  
Arash Mouradezadegun ◽  
Jafar Saghanezhad
Keyword(s):  
Sulfonic Acid ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Catalytic Amount ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
Short Time

The efficient one-pot condensation of aldehyde, dimedone, and phthalhydrazide has been achieved in the presence of a catalytic amount of phospho sulfonic acid as a novel environmentally benign heterogeneous solid acid under solvent-free conditions. A diversified 2H-indazolo[1,2-b]phthalazinetrione derivatives were prepared in good to excellent yields in short time. The economical factors (time, cost, waste etc.) for this three-component reaction hold promise for the future of organic synthesis.

scholarly journals Clean one-pot multicomponent synthesis of pyrans using a green and magnetically recyclable heterogeneous nanocatalyst

SynOpen ◽  
2021 ◽  
Author(s):  
Mina Ghassemi ◽  
Ali Maleki
Keyword(s):  
Room Temperature ◽  
Significant Loss ◽  
Copper Ferrite ◽  
Multicomponent Synthesis ◽  
Thermo Gravimetric ◽  
Sem Images ◽  
One Pot ◽  
Three Component Reaction ◽  
Ft Ir ◽  
The One

Copper ferrite (CuFe2O4) magnetic nanoparticles (MNPs) were synthesized via thermal decomposition method and applied as a reusable and green catalyst in the synthesis of functionalized 4H-pyran derivatives using malononitrile, an aromatic aldehyde and a β-ketoester in ethanol at room temperature. Then it was characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX) analysis, scanning electron microscopy (SEM) images, thermo gravimetric and differential thermo gravimetric (TGA/DTG) analysis. The catalyst was recovered from the reaction mixture by applying an external magnet and decanting the mixture. Recycled catalyst was reused for several times without significant loss in its activity. Running the one-pot three-component reaction at room temperature, no use of eternal energy source and using a green solvent provide benign, mild, and environmentally friendly reaction conditions; as well, ease of catalyst recovering, catalyst recyclability, no use of column chromatography and good to excellent yields are extra advantages of this work.

Silica sulfuric acid magnetic nanoparticle: an efficient and ecofriendly catalyst for synthesis of spiro[2-amino-4H-pyran-oxindole]s

2015 ◽  
Vol 93 (5) ◽  
pp. 546-549 ◽  
Author(s):  
Ali Reza Karimi ◽  
Meysam Sourinia ◽  
Zeinab Dalirnasab ◽  
Marzie Karimi
Keyword(s):  
Sulfuric Acid ◽  
Magnetic Nanoparticle ◽  
Ultrasound Irradiation ◽  
Significant Loss ◽  
Silica Sulfuric Acid ◽  
One Pot ◽  
External Magnet ◽  
Three Component Reaction ◽  
The One ◽  
High Yields

Silica sulfuric acid magnetic nanoparticles efficiently catalyze the one-pot, three-component reaction of isatins and malononitrile with dimedone, 1,3-dimethylbarbituric acid or 4-hydroxycoumarin in EtOH–H2O to afford the corresponding spiro[2-amino-4H-pyran-oxindole] derivatives in high yields under ultrasound irradiation at 60 °C. The heterogeneous nanocatalyst could be recovered easily from the reaction mixture using an external magnet and reused many times without significant loss of its catalytic activity.

One-pot synthesis of 3-aminofurans using a simple and efficient recyclable CuI/[bmim]PF6 system

2021 ◽  
Author(s):  
Guguloth Veeranna ◽  
Ramesh Balaboina ◽  
Narasimha Swamy Thirukovela ◽  
Ravindhar Vadde
Keyword(s):  
Secondary Amines ◽  
Terminal Alkynes ◽  
One Pot ◽  
One Pot Synthesis ◽  
System P ◽  
Three Component Reaction ◽  
The One

The one-pot three-component reaction of several 2-ketoaldehdyes, secondary amines and terminal alkynes to access 3-aminofurans was proceeded well in [bmim][PF6] using a simple and cheap CuI catalyst. The resulted 3-aminofuran...

Sulfated Tin Oxide: A Convenient Heterogeneous Catalyst for the Synthesis of 4-Arylmethylidene-3-substituted-isoxazol-5(4H)-ones

2021 ◽  
Vol 18 ◽  
Author(s):  
Nitishkumar S. Kaminwar ◽  
Sunil U. Tekale ◽  
Srinivas L. Nakkalwar ◽  
Rajendra P. Pawar
Keyword(s):  
Heterogeneous Catalyst ◽  
Tin Oxide ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Hydroxylamine Hydrochloride ◽  
One Pot ◽  
Easy Method ◽  
Three Component Reaction ◽  
Wide Range ◽  
The One

: Synthesis of isoxazole structural heterocyclic compounds is important due to their wide range of biological activities. In the present article, we report a convenient and easy method for the synthesis of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-ones by the one-pot three-component reaction of aldehydes, β-keto ester, and hydroxylamine hydrochloride cat-alyzed by sulfated tin oxide as a heterogeneous catalyst.

PTSA-Catalyzed One Pot Domino Synthesis of Dihydropyrido[2,3-d]pyrimidine Derivatives and their Antimicrobial Activity

2021 ◽  
Vol 6 (3) ◽  
pp. 222-227
Author(s):  
Krishna A. Bhensdadia ◽  
Prakash L. Kalavadiya ◽  
Nilam H. Lalavani ◽  
Shipra H. Baluja
Keyword(s):  
Antimicrobial Activity ◽  
Spectral Analysis ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
In Vitro Antimicrobial Activity ◽  
Aryl Aldehydes ◽  
Three Component Reaction ◽  
The One

A novel series of dihydropyrido[2,3-d]pyrimidine derivatives were synthesized by multicomponent domino cyclization via the one-pot three component reaction of 6-amino uracil, substituted aryl aldehydes and N-methyl-1-(methylthio)-2-nitroethenamine in the presence of PTSA 10 mol% as a catalyst. The structures of these synthesized compounds were characterized by spectral analysis. Further the synthesized compounds screened for in vitro antimicrobial activity. Among all the compounds, compound 4b containing flouro substitution exhibited good inhibition against the tested species.

scholarly journals A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

2019 ◽  
Vol 15 ◽  
pp. 1523-1533 ◽  
Author(s):  
András György Németh ◽  
György Miklós Keserű ◽  
Péter Ábrányi-Balogh
Keyword(s):  
Elemental Sulfur ◽  
Building Blocks ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
Synthetic Procedure ◽  
Three Component Reaction ◽  
Wide Range ◽  
Organic Chemist ◽  
The One

A new multicomponent reaction has been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of isothiocyanates, as valuable building blocks from isocyanides and sulfur is proposed, as well. The synthetic procedure suits the demand of a modern organic chemist, as it tolerates a wide range of functional groups, it is atom economic and easily scalable.

TiO2 Nanoparticles as an Efficient Catalyst for the One-pot Preparation of Tetrahydrobenzo[c]acridines in Aqueous Media

2013 ◽  
Vol 68 (4) ◽  
pp. 362-366 ◽  
Author(s):  
Shahrzad Abdolmohammadi ◽  
Mahdieh Mohammadnejad ◽  
Faezeh Shafaei
Keyword(s):  
Ammonium Acetate ◽  
Titanium Dioxide Nanoparticles ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
One Pot ◽  
Efficient Catalyst ◽  
The One ◽  
Work Up ◽  
Operational Simplicity

A series of tetrahydrobenzo[c]acridinone derivatives have been prepared by a one-pot fourcomponent reaction of 1-naphthol, aromatic aldehydes, dimedone, and ammonium acetate in aqueous media using a catalytic amount of titanium dioxide nanoparticles (TiO2 NPs). The advantages of this novel protocol include the excellent yields, operational simplicity, short reaction time, easy work-up, reusability of the catalyst and an environmentally friendly procedure.

scholarly journals Microwave Assisted Three Component Reaction Conditions to Obtain New Thiazolidinones with Different Heterocyclic Skeletons

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 38
Author(s):  
Fernando J. Lorenzo ◽  
Romina A. Ocampo ◽  
Sandra D. Mandolesi
Keyword(s):  
Microwave Irradiation ◽  
Thioglycolic Acid ◽  
Aldehyde Group ◽  
Green Solvent ◽  
Reaction Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Microwave Assisted ◽  
Three Component Reaction ◽  
The One

We present here a new proposal for the “one pot” generation of new 4-thiazolidinones (9a–e) through a multicomponent reaction under microwave irradiation conditions, using aromatic and heteroaromatic amines (8a–e), absolute ethanol as a “green” solvent and modifying the aldehyde group in the glycosidic residue, synthesized from D-mannitol. The study is focused in the variation of the irradiation times and the concentration of thioglycolic acid in order to study the possibility of controlling the structure and/or stereochemistry of the products formed in the reaction. Thiazolidinones 9a–d were obtained with a 69–82% The generation of the corresponding reaction products were monitored by TLC and CG-MS, taking reaction aliquots. The conditions reaction proved to be chemoselective depending on the excess of acid and irradiation times.

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