scholarly journals Greener and efficient one-pot synthesis of novel multi-substituted 3-(4,5-diphenyl-1H-imidazol-2-yl)-1H-indole derivatives by using recyclable catalyst under microwave irradiation

2021 ◽  
pp. 261-270 ◽  
Author(s):  
Narendra Nirwan ◽  
Chandresh Pareek
Keyword(s):  
Cost Effectiveness ◽  
Microwave Irradiation ◽  
Ammonium Acetate ◽  
Mass Spectrometric ◽  
Recyclable Catalyst ◽  
The Novel ◽  
Indole Derivatives ◽  
Time Cost ◽  
One Pot ◽  
Short Reaction Time

The novel class of multi-substituted indolylimidazole derivatives series substituted 3-(4,5-diphenyl-1H-imidazol-2-yl)-1H-indole and substituted 5-bromo-3-(4,5-diphenyl-1H-imidazol-2-yl)-1H-indole was synthesized utilising a green and efficient one-pot four components condensation of indole-3-carbaldehyde, benzil, ammonium acetate and various amines under microwave irradiation using Amberlyst A-15 as a recyclable catalyst. The catalyst Amberlyst A-15 has recovered from the reaction mixture and reused repeatedly for the next reaction. The key advantage of this process involves eco-friendly, very short reaction time, cost-effectiveness with the reusability of catalyst, easy workup, and purification of the product with excellent yields. FTIR, 1HNMR and Mass spectrometric studies analyzed and established the structures of all newly synthesized compounds.

Reactions of Methyl Ketones and (Hetero)arylcarboxamides with N,N-Dimethylacetamide Dimethyl Acetal. A Simple Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines

2015 ◽  
Vol 68 (2) ◽  
pp. 184 ◽  
Author(s):  
Benjamin Prek ◽  
Uroš Grošelj ◽  
Marta Kasunič ◽  
Silvo Zupančič ◽  
Jurij Svete ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Single Crystal ◽  
Ammonium Acetate ◽  
Dimethyl Acetal ◽  
Methyl Ketones ◽  
Closed Vessel ◽  
Simple Metal ◽  
One Pot ◽  
X Ray ◽  
Metal Free

Two metal-free syntheses of 2,4,6-trisubstituted pyridines 10a–m and 16a–j are described. N,N,6-Trimethyl-4-(substituted)pyridin-2-amines 10 were prepared from aryl or heteroaryl methyl ketones which were transformed with N,N-dimethylacetamide dimethyl acetal (DMADMA) into enaminones 4a–m, followed by treatment with ammonium acetate to give (Z)-3-amino-1-(substituted)but-2-en-1-ones 5a–m. These were treated with DMADMA under microwave irradiation in a closed vessel at 130°C, to give via intermediates 7–9 the final products 10a–m. N2,N2,N4,N4-Tetramethyl-6-(substituted) pyridine-2,4-diamines 16a–j were prepared in a one-pot synthesis from the corresponding carboxamides 11a–j by treatment with an excess of DMADMA in a closed vessel under microwave irradiation to give via intermediates 12a–j to 15a–j the final products 16a–j. X-Ray single crystal diffractometry studies of the enaminones 5c, 5g, 5i, 5j, and 5m and 2,4,6-trisubstituted pyridines 16a, 16b, 16g, 16i, and 16j were consistent with the expected structures.

Tributylhexadecylphosphonium bromide: an efficient reagent system for the one-pot synthesis of 2,4,5-trisubstituted imidazoles

2015 ◽  
Vol 21 (2) ◽  
Author(s):  
Mohammad Heidari ◽  
Mohsen Rezaei ◽  
Rashid Badri
Keyword(s):  
Cost Effectiveness ◽  
Aromatic Aldehyde ◽  
Ammonium Acetate ◽  
Reaction Times ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Efficient Reagent

AbstractThe reaction of benzil, an aromatic aldehyde, and ammonium acetate in ethanol at reflux in the presence of tributylhexadecylphosphonium bromide as catalyst affords a 2,4,5-trisubstituted imidazole. The present methodology offers several advantages over the literature methods, including excellent yields, shorter reaction times, environmentally benign milder reaction conditions, cost-effectiveness of catalyst, easy workup, and purification of products by nonchromatographic methods.

Multi-component synthesis of highly substituted imidazoles catalyzed by nanorod vanadatesulfuric acid

2015 ◽  
Vol 69 (11) ◽  
Author(s):  
Masoud Nasr-Esfahani ◽  
Morteza Montazerozohori ◽  
Tooba Abdizadeh
Keyword(s):  
Reaction Time ◽  
High Purity ◽  
Ammonium Acetate ◽  
Chlorosulfonic Acid ◽  
Solvent Free ◽  
One Pot ◽  
Short Reaction Time ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Tetrasubstituted Imidazoles

AbstractNanorod vanadatesulfuric acid (VSA NRs), as a recyclable and eco-benign catalyst, was used for one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles using aldehydes, benzil, benzoin or 9,10-phenanthrenequinone and ammonium acetate or aniline under solvent-free conditions providing high to excellent yields. VSA is easily prepared by a simple reaction of chlorosulfonic acid and sodium metavanadate in high purity. As compared with the conventional procedures, the present protocol offers several advantages such as simplicity of procedure, short reaction time, high yields, easy workup, recoverability and reusability of the catalyst and simple purification of the products.

Rh(iii)-catalyzed C–H activation reactions forming 1H-isoindoles containing a quaternary carbon center from aryl ketones or benzylamines

2016 ◽  
Vol 52 (66) ◽  
pp. 10171-10174 ◽  
Author(s):  
Yeonhui Yi ◽  
Hyejeong Lee ◽  
Chul-Ho Jun
Keyword(s):  
Microwave Irradiation ◽  
Ammonium Acetate ◽  
Quaternary Carbon ◽  
One Pot ◽  
Aryl Ketones ◽  
Acrylate Esters

Rh(iii)/Cu(OAc)2 catalyzed, one-pot reactions of aryl ketones, acrylate esters and ammonium acetate or α-substituted benzylamines under microwave irradiation conditions produce 1H-isoindoles bearing a quarternary carbon center.

Magnetically separable graphene oxide anchored sulfonic acid: a novel, highly efficient and recyclable catalyst for one-pot synthesis of 3,6-di(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles in deep eutectic solvent under microwave irradiation

RSC Advances ◽  
2016 ◽  
Vol 6 (108) ◽  
pp. 106160-106170 ◽  
Author(s):  
Mo Zhang ◽  
Peng Liu ◽  
Yu-Heng Liu ◽  
Ze-Ren Shang ◽  
Hai-Chuan Hu ◽  
...  
Keyword(s):  
Graphene Oxide ◽  
Microwave Irradiation ◽  
Sulfonic Acid ◽  
Deep Eutectic Solvent ◽  
Acid Catalyst ◽  
Recyclable Catalyst ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
Magnetically Separable

A magnetic separable sulfonic acid catalyst was prepared and applied for the synthesis of 3,6-di(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles via three-component reaction of 1-phenyl-3-(pyridin-3-yl)-1H-pyrazol-5-amine, β-ketonitrile and aldehydes in DES.

A Facile Procedure for Synthesis of Several 1, 4, 5-Trisubstituted-1Himidazole- 2(3H)-ones and -thiones via a One-pot Three-portion Reaction in Solvent and Microwave Irradiation

2019 ◽  
Vol 16 (2) ◽  
pp. 104-109
Author(s):  
Mohammad Shaker
Keyword(s):  
Acetic Acid ◽  
Microwave Irradiation ◽  
Glacial Acetic Acid ◽  
Ammonium Acetate ◽  
Fluorescence Properties ◽  
Irradiation Condition ◽  
One Pot ◽  
Three Component Reaction

An ordinary procedure for the synthesis of several 1, 4, 5-trisubstituted-1H-imidazole- 2(3H)-ones and -thiones by a one-pot three-component reaction of glacial acetic acid under solvent, microwave irradiation condition is proposed. The products were formed through cyclization of benzoin with isothiocyanates or isocyanates and ammonium acetate. All incorporated combinations were determined for their spectral and microanalytical information. These compounds were subsequently studied for their fluorescence properties.

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