Copper-catalyzed one-pot synthesis of benzimidazole derivatives

2008 ◽  
Vol 86 (11) ◽  
pp. 1044-1051 ◽  
Author(s):  
Hashem Sharghi ◽  
Mona Hosseini-Sarvari ◽  
Fatemeh Moeini
Keyword(s):  
Heterogeneous Catalyst ◽  
Simple Procedure ◽  
Catalytic Reactions ◽  
Environmentally Benign ◽  
Benzimidazole Derivatives ◽  
Good Recovery ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Mild Conditions ◽  
High Yields

A simple, efficient, and environmentally benign method has been developed for the synthesis of 2-substituted benzimidazoles through a one-pot reaction of phenylenediamines with aryl aldehydes in excellent isolated yields under mild conditions using Cu(II) complex as the selective, recyclable, and heterogeneous catalyst at ambient temperature. The Cu(II) complex as a heterogeneous catalyst can be reused in further catalytic reactions, and it was found that its activity remained largely unchanged for eight successive runs. No metal-complex leaching was observed after the consecutive catalytic reactions. The salient features of this method include mild conditions, high yields, simple procedure, and good recovery and reusability of the heterogeneous catalyst.Key words: benzimidazole, o-phenylenediamine, arylaldehydes, heterogeneous catalyst, N,N-bis (2-hydroxyphenyl)pyridine-2,6-dicarboxamide.

scholarly journals An Efficient and Green Procedure for the Synthesis of 2,4,6-Triarylpyridines Using PPA-SiO2as a Reusable Heterogeneous Catalyst Under Solvent-Free Conditions

2012 ◽  
Vol 9 (4) ◽  
pp. 2037-2043 ◽  
Author(s):  
Abolghasem Davoodnia ◽  
Bahareh Razavi ◽  
Niloofar Tavakoli-Hoseini
Keyword(s):  
Heterogeneous Catalyst ◽  
Simple Procedure ◽  
Substantial Reduction ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
High Yields ◽  
Work Up

Silica gel-supported polyphosphoric acid (PPA-SiO2) was found to be highly efficient, eco-friendly and recyclable heterogeneous catalyst for the synthesis of 2,4,6-triarylpyridines through one-pot three-component reaction of acetophenone, aryl aldehydes, and ammonium acetate under solvent-free conditions. This method has several advantages, such as simple procedure with an easy work-up, short reaction times, and high yields. Furthermore, the catalyst could be recycled after a simple work-up, and used at least three times without substantial reduction in its catalytic activity.

One-pot synthesis of 2-amino-3-cyano-4-arylsubstituted tetrahydrobenzo[b]pyrans catalysed by silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst

2011 ◽  
Vol 65 (5) ◽  
Author(s):  
Abolghasem Davoodnia ◽  
Sadegh Allameh ◽  
Samineh Fazli ◽  
Niloofar Tavakoli-Hoseini
Keyword(s):  
Reaction Time ◽  
Silica Gel ◽  
Convenient Method ◽  
Polyphosphoric Acid ◽  
Simple Procedure ◽  
Reusable Catalyst ◽  
One Pot ◽  
Short Reaction Time ◽  
Aryl Aldehydes ◽  
High Yields

AbstractA convenient method for the synthesis of tetrahydrobenzo[b]pyrans by a one-pot three-component cyclocondensation of dimedone, aryl aldehydes, and malononitrile in water using silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst is described. The present methodology offers several advantages, such as a simple procedure with ease of handling, short reaction time, high yields, and the absence of any volatile and hazardous organic solvents.

scholarly journals Scolecite as an efficient heterogeneous catalyst for the synthesis of 2,4,5-triarylimidazoles

2009 ◽  
Vol 7 (3) ◽  
pp. 550-554 ◽  
Author(s):  
Lakshman Gadekar ◽  
Shivshankar Mane ◽  
Santosh Katkar ◽  
Balasaheb Arbad ◽  
Machhindra Lande
Keyword(s):  
Heterogeneous Catalyst ◽  
Ammonium Acetate ◽  
Environmentally Benign ◽  
One Pot ◽  
Effective Catalyst ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Efficient Heterogeneous Catalyst

AbstractNatural scolecite has been found as an effective catalyst for the one-pot synthesis of 2,4,5-triarylimidazole derivatives via a three component reaction using benzil or benzoin, aldehydes and ammonium acetate. This method provides several advantages such as being environmentally benign, reusable, possessing high yields with increased variations of the substituents in the product and preparative simplicity.

scholarly journals Phosphosulfonic acid, an efficient solid acid catalyst for the one-pot preparation of 14-aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes under solvent-free conditions

2013 ◽  
Vol 78 (9) ◽  
pp. 1291-1299 ◽  
Author(s):  
Reza Kiasat ◽  
Arash Mouradzadegun ◽  
Jafar Saghanezhad
Keyword(s):  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

An expeditious procedure for the synthesis of 14- aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes through one-pot pseudo three component condensation of ?-naphthol or dimedone with various aryl aldehydes is described. This greener protocol is catalyzed by phosphosulfonic acid, and proceeds efficiently in the absence of any organic solvent under optimized, mild, green and environmentally benign reaction conditions in high yields within 20-55 minutes.

scholarly journals An Atom Economic Acid Catalyzed Synthetic Method for Aromatic Imines

2017 ◽  
Vol 2 (1) ◽  
pp. 6 ◽  
Author(s):  
Shyamal Baruah ◽  
Alexander Fisyuk ◽  
Ivan V. Kulakov ◽  
Amrit Puzari
Keyword(s):  
Simple Procedure ◽  
Acid Catalyst ◽  
Environmentally Benign ◽  
One Pot ◽  
Mild Conditions ◽  
Benign Nature ◽  
Higher Temperature ◽  
Acid Catalyzed ◽  
Aromatic Imines ◽  
Byproduct Formation

A new one-pot acid catalyzed synthetic methodology has been described for synthesis of aromatic imines. The reaction is carried out under microwave irradiation using minimum amount of methanol as solvent. Aqueous solution of the acid catalyst act as solvent for amine dissolution. The reaction yields substantial yield of product imine. The simplicity and environmentally benign nature of the process are the most notable features. The process can also be extended to include wide number of substrates. Product of the reaction can be isolated by simple procedure. The reaction can be carried out under mild conditions without heating to a higher temperature which eventually prevents the formation of nitrile byproducts in the reaction. Byproduct formation was significantly less during the reaction.

A concise and efficient CuI-catalyzed synthesis of diimino dihydroquinazoline derivatives from isocyanides and guanidines derivatives through intramolecular C–H activation

2021 ◽  
Vol 18 ◽  
Author(s):  
Manijeh Nematpour ◽  
Hossein Fasihi Dastjerdi ◽  
Mohammad Mahboubi-Rabbani
Keyword(s):  
Mechanistic Explanation ◽  
Analysis Data ◽  
Environmentally Benign ◽  
Elemental Analysis Data ◽  
One Pot ◽  
Activation Reaction ◽  
Short Reaction Time ◽  
Mass Spectral ◽  
Mild Conditions ◽  
High Yields

: A novel series of diimino dihydroquinazoline derivatives were synthesized from isocyanides and guanidine analogs in quantitative yields by applying an efficient, inexpensive, one-pot copper-catalyzed intramolecular C-H activation reaction under mild conditions. The structures were confirmed on the basis of IR, 1HNMR, 13C NMR, mass spectral and elemental analysis data. The protocol offers advantages like short reaction time, simple workup process, high yields, and an environmentally benign methodology. Interestingly, better results (yield = 82%) were observed in terms of the yield obtained by using a mixture of CuI, Cs2CO3 and acetonitrile as the catalyst, base and solvent, respectively. The data also suggested that compound 5i is produced with the highest yield (87%) from the corresponding diisopropyl carbon diimide, 4-nitroaniline and phenyl isocyanide. Finally, a mechanistic explanation for the reaction promoted by cuprous iodide (CuI) was proposed on the basis of previous investigations and our experimental observations.

scholarly journals Synthesis of 2,4,6-triarylpyridines Using AlPO4 Under Solvent-free Conditions

2010 ◽  
Vol 2 (2) ◽  
pp. 337-342 ◽  
Author(s):  
P. Rajput ◽  
N. J. P. Subhashini ◽  
Shiva Raj
Keyword(s):  
Heterogeneous Catalyst ◽  
Simple Procedure ◽  
Reaction Times ◽  
Aluminum Phosphate ◽  
Solvent Free ◽  
One Pot ◽  
One Pot Synthesis ◽  
Solvent Free Conditions

A series of 2,4,6-triarylpyridines have been prepared using a variety of aromatic and heteroaromatic aldehydes in the presence of aluminum phosphate (AlPO4) as a heterogeneous catalyst at 120 oC under solvent-free conditions. The present methodology offers several advantages such as excellent yields, simple procedure, shorter reaction times, milder conditions and the catalyst exhibited remarkable reusable activity. Keywords: Aluminum phosphate; 2,4,6-triarylpyridines; One-pot synthesis; Shorter reaction times;  Reusable activity.  © 2010 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved. DOI: 10.3329/jsr.v2i2.3859               J. Sci. Res. 2 (2), 337-342 (2010) 

Catalytic application of SO42−/Fe–ZrO2nanoparticles synthesized by a urea hydrolysis method for environmentally benign one pot synthesis of 1,8-dioxodecahydroacridines

RSC Advances ◽  
2015 ◽  
Vol 5 (105) ◽  
pp. 86179-86190 ◽  
Author(s):  
Sagnika Pradhan ◽  
B. G. Mishra
Keyword(s):  
Heterogeneous Catalyst ◽  
Mixed Oxides ◽  
Urea Hydrolysis ◽  
Environmentally Benign ◽  
One Pot ◽  
Hydrolysis Method ◽  
One Pot Synthesis ◽  
Catalytic Application

A series of sulfate grafted Fe2O3–ZrO2mixed oxides (SFexZr) were prepared by urea hydrolysis method and studied as heterogeneous catalyst for synthesis of structurally diverse 1,8-dioxodecahydroacridines.

An efficient one pot three-component nanocatalyzed synthesis of spiroheterocycles using TiO2 nanoparticles as a heterogeneous catalyst

RSC Advances ◽  
2015 ◽  
Vol 5 (57) ◽  
pp. 46415-46422 ◽  
Author(s):  
Yogesh Kumar Tailor ◽  
Sarita Khandelwal ◽  
Yogita Kumari ◽  
Kamlendra Awasthi ◽  
Mahendra Kumar
Keyword(s):  
Tio2 Nanoparticles ◽  
Heterogeneous Catalyst ◽  
Environmentally Benign ◽  
One Pot

An efficient, environmentally benign isocyanide-based domino protocol is presented for synthesizing spiroheterocycles with 2-amino benzothiazole/1,3,4-thiadiazole, cyclohexyl/tert-butyl isocyanides and isatines/cyclic carbonyls, catalyzed by recyclable nanocrystalline TiO2.

Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium Phthalimide-N-oxyl

Synthesis ◽  
2020 ◽  
Vol 52 (11) ◽  
pp. 1707-1718
Author(s):  
Nasser Etivand ◽  
Jabbar Khalafy ◽  
Mohammad G. Dekamin
Keyword(s):  
Aqueous Media ◽  
Thiobarbituric Acid ◽  
Environmentally Benign ◽  
The Novel ◽  
One Pot ◽  
Synthetic Strategy ◽  
Three Component Reaction ◽  
High Yields ◽  
Green Procedure ◽  
Arylglyoxal Monohydrates

A simple, clean, straightforward, and environmentally benign one-pot, three-component reaction of various arylglyoxal monohydrates, β-naphthol, and barbituric acid [pyrimidine-2,4,6(1H,3H,5H)-trione] or thiobarbituric acid in the presence of catalytic amounts potassium phthalimide-N-oxyl (PPINO), as a mild and efficient organocatalyst in aqueous media under reflux conditions is reported. This transformation produced the novel diverse-substituted 12-benzoyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-diones and their sulfur analogues in 82–93% yield via filtration and without utilization of any chromatography. The high yields of products, very simple operation, easy workup, availability of starting materials, green process, and high atom-economy are the main benefits of this synthetic strategy.

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