Highly stereoselective facile synthesis of β-amino carbonyl compounds via a Mannich-type reaction catalyzed by γ-Al2O3/MeSO3H (alumina/methanesulfonic acid: AMA) as a recyclable, efficient, and versatile heterogeneous catalyst

2010 ◽  
Vol 88 (1) ◽  
pp. 14-26 ◽  
Author(s):  
Hashem Sharghi ◽  
Mahboubeh Jokar
Keyword(s):  
Heterogeneous Catalyst ◽  
Mannich Reaction ◽  
Carbonyl Compounds ◽  
Methanesulfonic Acid ◽  
Aromatic Aldehydes ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Environmentally Conscious ◽  
Catalytic Activities ◽  
First Time

Mannich reaction of ketones, aromatic aldehydes, and aromatic amines catalyzed efficiently by γ-Al2O3/MeSO3H (alumina/methanesulfonic acid: AMA) as a heterogeneous catalyst, which were carried out in EtOH at ambient temperature to afford the corresponding β-amino ketones in good yields and high stereoselectivities in favor of the anti isomer, was described for the first time. It was found that this catalyst could be completely recovered and reused without loss of its catalytic activities and is thus environmentally conscious. Furthermore, the use of γ-Al2O3/CH3SO3H (AMA) catalyst is feasible because of its easy preparation, easy handling, stability, easy recovery, reusability, good activity, stereoselectivity, and eco-friendliness. The use of this method provides a novel and improved modification of the three-component Mannich reaction in terms of mild reaction conditions and clean reaction profiles, using a very small quantity of catalyst and a simple workup procedure.

scholarly journals Direct use of mineral fertilizers MAP, DAP, and TSP as heterogeneous catalysts in organic reactions

2016 ◽  
Vol 5 (6) ◽  
pp. 615-623 ◽  
Author(s):  
Imane Bahammou ◽  
Ayoub Esaady ◽  
Said Boukhris ◽  
Rachida Ghailane ◽  
Nouzha Habbadi ◽  
...  
Keyword(s):  
Heterogeneous Catalysts ◽  
Knoevenagel Condensation ◽  
Aromatic Aldehydes ◽  
Significant Loss ◽  
Mineral Fertilizers ◽  
Phosphate Fertilizers ◽  
Reaction Conditions ◽  
Catalytic Activities ◽  
First Time ◽  
Direct Use

In this paper, we reported the first use of phosphate fertilizers (MAP, DAP, and TSP) as heterogeneous catalysts for organic reactions.  Their catalytic activities were investigated in the first time in Knoevenagel condensation of various aromatic aldehydes with malononitrile at room temperature.  These minerals phosphate showed high catalytic activities and ability to be recovering and reusing without a significant loss in their catalytic activities.  In order to reach the optimal reaction conditions for Knoevenagel condensation, we carried out a kinetic study of the effect of reaction time, the effect of solvent, the amount of catalysts and the variation of the range of the particles size the more active.  The best conditions were obtained by the use of these fertilizers (MAP, DAP, and TSP) in their commercial status, simply crashed in powder, without any purification, using ethanol as solvent.  These phosphate fertilizers prove to be very promising and effective heterogeneous catalysts for the condensation of Knoevenagel.

A Novel Environment Friendly Material: Sucrose Char Sulfonic Acid Catalyzed Three-Component Mannich Reaction

2014 ◽  
Vol 989-994 ◽  
pp. 134-137
Author(s):  
Yuan Yuan She ◽  
Xuan Yan Liu ◽  
Zhi Gao Yang
Keyword(s):  
Mannich Reaction ◽  
Carbonyl Compounds ◽  
Sulfonic Acid ◽  
Aromatic Aldehydes ◽  
Reaction Conditions ◽  
One Pot ◽  
Environment Friendly ◽  
Novel Environment ◽  
Acid Catalyzed ◽  
The One

Sucrose char sulfonic acid (SCSA) efficiently catalyzed the one-pot, three-component Mannich reaction of ketones, aromatic aldehydes and different amines in ethanol at 30°C and afforded the corresponding β-amino carbonyl compounds in good to excellent yields . This method provides a novel and improved modification of the three-component Mannich reaction in terms of mild reaction conditions , clean reaction profiles and a simple workup procedure.

DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110458
Author(s):  
Le Nhat Thuy Giang ◽  
Dang Thi Tuyet Anh ◽  
Hoang Thi Phuong ◽  
Nguyen Ha Thanh ◽  
Nguyen Thi Quynh Giang ◽  
...  
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Basic Catalyst ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Short Reaction Time ◽  
Convenient Approach ◽  
First Time

For the first time the 4-dimethylaminopyridine (DMAP) catalyzed straightforward and efficient procedure has been developed for the synthesis of 3,3′-(arylmethylene) bis(2-hydroxynaphthalene-1,4-dione) derivatives starting from lawsone (2-hydroxy-1,4-naphthoquinone) and a variety of (hetero)aromatic aldehydes in ethanol under microwave irradiation. Three of nine synthesized compounds are new. This method provides notable advantages over existing procedures including use of non-traditional basic catalyst and environmentally benign solvent, mild reaction conditions, excellent yields, short reaction time and simple workup.

Three-component Reaction of Cycloheptanone, 6-Amino-1,3-Dimethyluracil and Aromatic Aldehydes; X-Ray Structure, and Anti-inflammatory Evaluation of the Products

2008 ◽  
Vol 63 (9) ◽  
pp. 1117-1126 ◽  
Author(s):  
Mohamed I. Hegab ◽  
Nasser A. Hassan ◽  
Farouk M. E. Abdel-Megeid
Keyword(s):  
Schiff Bases ◽  
Aromatic Aldehydes ◽  
X Ray Diffraction ◽  
Nmr Studies ◽  
Reaction Conditions ◽  
X Ray ◽  
Three Component Reaction ◽  
The Given ◽  
First Time ◽  
C Nmr

1,3-Dimethyl-5-aryl-1,6,7,8,9,10-hexahydrocyclohepta[5,6]pyrido[2,3-d]pyrimidine-2,4-diones 4a, b (the linear regioisomers) and the Schiff bases, 6-N-benzylidenamino-1,3-dimethyluracil derivatives 5a, b, were isolated from a three-component reaction of cycloheptanone, 6-amino-1,3- dimethyluracil, and 4-chloro- or 4-bromobenzaldehyde. Surprisingly, 1,3-dimethyl-10-aryl-1,5,6,7, 8,9-hexahydrocyclohepta[4,5]pyrido-[2,3-d]pyrimidine-2,4-diones 6f, g (the angular regioisomers which are described for the first time in the literature under the given reaction conditions) and the Schiff bases, 6-N-benzylidenamino-1,3-dimethyluracil derivatives 5f, g, were isolated and characterized from the reaction with 4-methoxybenzaldehyde and 4-cyanobenzaldehyde. However, the three-component reaction of 6-amino-1,3-dimethyluracil, cycloheptanone, and 2-methoxybenzaldehyde afforded 1,3-dimethylbenzo[4,5]pyrido[3,2-d]pyrimidine-3,4-dione (7). Single crystal X-ray diffraction and 13C NMR studies of 4a and 6f provided support for the established structures. Some of the new products were tested for antiinflammatory activity comparable to indomethacin.

ChemInform Abstract: Carbon-Based Solid Acid Catalyzed One-Pot Mannich Reaction: A Facile Synthesis of β-Amino Carbonyl Compounds.

ChemInform ◽  
2011 ◽  
Vol 42 (28) ◽  
pp. no-no
Author(s):  
Abolghasem Davoodnia ◽  
Afsaneh Tavakoli-Nishaburi ◽  
Niloofar Tavakoli-Hoseini
Keyword(s):  
Mannich Reaction ◽  
Carbonyl Compounds ◽  
Solid Acid ◽  
Facile Synthesis ◽  
One Pot ◽  
Acid Catalyzed ◽  
Carbon Based

One-pot synthesis of β-amino carbonyl compounds catalyzed silica supported phenylphosphinic acid

2015 ◽  
Vol 4 (1) ◽  
Author(s):  
Di Liu ◽  
Jingwei Zhang ◽  
Chi Zhang ◽  
Xiaoyan Kou
Keyword(s):  
Cost Efficiency ◽  
Carbonyl Compounds ◽  
Aromatic Aldehydes ◽  
Reusable Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Environment Friendly ◽  
Aliphatic Ketones ◽  
One Pot Condensation ◽  
The One

AbstractA simple and facile synthesis of β-amino carbonyl compounds was developed by the one-pot condensation of cyclohexanone, aromatic aldehydes and anilines at 25°C in the presence of silica supported phenylphosphinic acid. β-Amino carbonyl compounds were obtained in moderate to good yields and reasonable diastereoselectivities. This method has the advantages of short reaction time, mild reaction conditions, reusable catalyst, cost efficiency and environment friendly. In addition, acetophenone and aliphatic ketones as reactants were investigated.

scholarly journals Microwave-Induced Montmorillonite-Mediated Facile Synthesis of Enamines

2019 ◽  
Vol 32 (2) ◽  
pp. 249-254
Author(s):  
Ram Naresh Yadav ◽  
Indrani Banik ◽  
Ashok Kumar Srivastava ◽  
Katherine Ramos ◽  
Bimal Krishna Banik
Keyword(s):  
Reaction Time ◽  
Carbonyl Compounds ◽  
Montmorillonite Clay ◽  
Secondary Amines ◽  
High Yield ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Cyclic Amines

Montmorillonite clay-mediated simple and high yielding protocol for the synthesis of various enamines with secondary amines and ketones is developed under microwave condition. This protocol is very convenient to accesses the enamines from cyclic amines with various carbonyl compounds in high yield under mild reaction conditions with short reaction time.

Efficient cyclodehydration of diethylene glycol in Brønsted acidic ionic liquids

2008 ◽  
Vol 62 (3) ◽  
Author(s):  
Yuan-Yuan Wang ◽  
Wei Li ◽  
Li-Yi Dai
Keyword(s):  
Ionic Liquids ◽  
Diethylene Glycol ◽  
Molar Ratio ◽  
Temperature Reaction ◽  
Hydrogen Sulfate ◽  
Optimum Conditions ◽  
Reaction Conditions ◽  
Catalytic Activities ◽  
Acidic Ionic Liquids ◽  
First Time

AbstractCyclodehydration of diethylene glycol using various Brønsted acidic ionic liquids as dual solvent-catalysts has been studied for the first time. Better results were obtained in the presence of 1-butyl-3-methylimidazolium hydrogen sulfate ([PSmim]HSO4) compared with other Brønsted acidic ionic liquids. Effects of the reaction conditions such as reaction temperature, reaction time and molar ratio of ionic liquid to diethylene glycol have been investigated. High diethylene glycol conversion, 97.0 %, and high 1,4-dioxane selectivity, 89.3 %, were obtained in [PSmim]HSO4 under optimum conditions. Hammett method was used to determine the acidity order of these ionic liquids and the results were consistent with the catalytic activities observed in the cyclodehydration reaction. Utilization of Brønsted acidic ionic liquids as dual solvent-catalysts has some advantages, e.g. high conversion of DEG, easy preparation and reuse of ionic liquids, avoiding toxic catalysts and solvents.

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