Ultrasound-assisted rapid synthesis of β-aminoketones with direct-type catalytic Mannich reaction using bismuth(III) triflate in aqueous media at room temperature

2012 ◽  
Vol 66 (1) ◽  
Author(s):  
S. Ozturkcan ◽  
Kadir Turhan ◽  
Zuhal Turgut
Keyword(s):  
Reaction Time ◽  
Mannich Reaction ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Rapid Synthesis ◽  
Low Toxicity ◽  
Ultrasound Assisted ◽  
Easy Operation

AbstractAn innovative, powerful, efficient and relatively rapid method was developed to synthesise various β-aminoketone derivatives from cyclohexanone, substituted aromatic amines and aromatic or hetero-aromatic aldehydes via ultrasound-assisted direct-type catalytic Mannich reaction using bismuth(III) triflate in water. Good yields of the desired β-aminoketones were obtained at room temperature by ultrasound-assisted reaction within 1–2 h. The major advantages of the proposed method are undemanding conditions, easy operation, low toxicity, shorter reaction time, anti selectivity and higher yields in comparison with conventional methods.

One-pot three-component Mannich reaction in water catalyzed by eco-friendly, hydrophobic and recyclable sulfonic acid based nanosilica (SBA-15-Ph-PrSO3H)

RSC Advances ◽  
2014 ◽  
Vol 4 (71) ◽  
pp. 37941-37946 ◽  
Author(s):  
Daryoush Zareyee ◽  
Hamidreza Alizadeh
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Sulfonic Acid ◽  
Room Temperature ◽  
Aromatic Aldehydes ◽  
Green Method ◽  
One Pot ◽  
The Mannich Reaction ◽  
Reaction In Water

A mild, effective and green method for the Mannich reaction of aromatic aldehydes, aromatic amines and ketones has been accomplished in good to excellent yields using hydrophobic SBA-15-Ph-PrSO3H in water at room temperature.

The Mannich Reaction Between Aromatic Ketones, Aromatic Aldehydes and Aromatic Amines

Synthesis ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 717-718 ◽  
Author(s):  
Yi Lin ◽  
Lei Huangshu ◽  
Zou Junhua ◽  
Xu Xiujuan
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Aromatic Aldehydes ◽  
Aromatic Ketones ◽  
The Mannich Reaction

SiO2·12WO3·24H2O: a Highly Efficient Catalyst for the Synthesis of 5-Arylidene Barbituric Acid in the Presence of Water

2009 ◽  
Vol 62 (4) ◽  
pp. 353 ◽  
Author(s):  
Ji-Tai Li ◽  
Ming-Xuan Sun
Keyword(s):  
Room Temperature ◽  
Barbituric Acid ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Efficient Route ◽  
Acid Catalyzed ◽  
High Yields

The condensation of aromatic aldehydes and barbituric acid catalyzed by SiO2·12WO3·24H2O in aqueous media at room temperature gave 5-arylidene barbituric acid in high yields with or without the use of ultrasound, providing a simple and efficient route to synthesis of these compounds.

An operationally simple green procedure for the synthesis of dihydropyrimido[4,5-d]pyrimidinetriones using CuI nanoparticles as a highly efficient catalyst

2015 ◽  
Vol 70 (3) ◽  
pp. 171-176 ◽  
Author(s):  
Shahrzad Abdolmohammadi ◽  
Maryam Afsharpour
Keyword(s):  
Room Temperature ◽  
Aqueous Media ◽  
Coupling Reaction ◽  
Aromatic Aldehydes ◽  
Significant Loss ◽  
Efficient Catalyst ◽  
Nano Crystalline ◽  
Simple Protocol ◽  
High Yields ◽  
Green Procedure

AbstractA green, efficient and simple protocol was developed for the synthesis of dihydropyrimido[4,5-d]pyrimidinetrione derivatives via a coupling reaction of 6-aminouracils, aromatic aldehydes and urea in aqueous media in the presence of nano-crystalline CuI at room temperature. The products were obtained in high yields. CuI nanoparticles can be recycled three times without significant loss of catalytic activity.

Grinding Synthesis of Pyrazolyl-Bis Coumarinyl Methanes Using Potassium 2-Oxoimidazolidine-1,3-diide

2019 ◽  
Vol 16 (2) ◽  
pp. 303-308 ◽  
Author(s):  
Kazem Hematinezhad ◽  
Mohammad Nikpassand ◽  
Leila Zare Fekri
Keyword(s):  
Reaction Time ◽  
Room Temperature ◽  
Aqueous Media ◽  
13C Nmr Spectroscopy ◽  
Reusable Catalyst ◽  
Reduced Pressure ◽  
Elemental Analyses ◽  
Nucleophilic Addition Reaction ◽  
High Yields ◽  
Work Up

Aim and Objective: Potassium 2-oxoimidazolidine-1,3-diide (POImD) as a novel and reusable catalyst was used for the synthesis of pyrazolyl-bis coumarinyl methanes by a nucleophilic addition reaction of synthetized pyrazolecarbaldehyde and two equivalents of 4-hydroxycoumarin under grinding. The catalyst can be reused and recovered several times without loss of activity. This method provides several advantages such as eco-friendliness, simple work-up and shorter reaction time as well as excellent yields. All of the synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy and elemental analyses. Material and Method: Synthetized pyrazole carbaldehyde 1a (1 mmol), 4-hydroxycoumarin 2 (2 mmol), 1 mmol of POImD and 10mL of H2O were ground in a mortar by a pestle for 30-90 minutes. After the completion of the reaction, as monitored by TLC on silica gel using ethyl acetate/n-hexane (1:2), the mixture was allowed to cool to room temperature. After completion of the reaction, we extracted the product with CH2Cl2/H2O. This was followed by separation of phases, evaporation of the organic phase and recrystallization of the residue with 50 mL of ethanol/H2O (1:1). The pure product was then obtained in 87 to 96% yield. The aqueous phase was concentrated under reduced pressure to recover the catalyst for subsequent use. Results: To continue our ongoing studies to synthesize heterocyclic and pharmaceutical compounds by mild, facile and efficient protocols, herein we wish to report our experimental results on the synthesis of pyrazolylbis coumarinyl methanes, using various synthetized pyrazole carbaldehydes and 4-hydroxycoumarin in the presence of POImD in aqueous media at room temperature. Conclusion: Finally, we developed an efficient, fast and convenient procedure for the three-component synthesis of pyrazolyl-bis coumarinyl methanes through the reaction of pyrazole carbaldehydes and 4- hydroxycoumarin, using POImD as a novel and reusable catalyst. The remarkable advantage offered by this method is that the catalyst is non-toxic, inexpensive, easy to handle and reusable. A short reaction time, simple work-up procedure, high yields of product with better purity and the green aspect by avoiding a hazardous solvent and a toxic catalyst are the other advantages. To the best of our knowledge, this is the first report on the synthesis of pyrazolyl-bis coumarinylmethane derivatives using potassium 2-oxoimidazolidine-1,3-diide (POImD).

scholarly journals Trifluoroacetic Acid as an Efficient Catalyst for the Room Temperature Synthesis of 2-Aryl-1-arylmethyl-1H-1,3-benzimidazoles in Aqueous Media

2011 ◽  
Vol 8 (1) ◽  
pp. 101-106 ◽  
Author(s):  
Mohammad R. Mohammadizadeh ◽  
S. Zeinakhatoun Taghavi
Keyword(s):  
Trifluoroacetic Acid ◽  
Room Temperature ◽  
Condensation Reaction ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Temperature Synthesis ◽  
Efficient Catalyst ◽  
Room Temperature Synthesis ◽  
Effective Catalyst

Trifluoroacetic acid (TFA) is introduced as a commercially available, inexpensive and effective catalyst for the selective and eco-compatible synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazolesviacondensation reaction ofo-phenylenediamine derivatives and aromatic aldehydes in ethanol/water at room temperature.

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