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 A Green, Expeditious, One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones Using a Mixture of Phosphorus Pentoxide-Methanesulfonic Acid at Ambient Temperature

2012 ◽  
Vol 2012 ◽  
pp. 1-6 ◽  
Author(s):  
Amulrao Borse ◽  
Mahesh Patil ◽  
Nilesh Patil ◽  
Rohan Shinde
Keyword(s):  
Reaction Time ◽  
Ambient Temperature ◽  
Room Temperature ◽  
Simple Procedure ◽  
Methanesulfonic Acid ◽  
Phosphorus Pentoxide ◽  
One Pot ◽  
Short Reaction Time ◽  
Solvent Free Conditions ◽  
High Yields

An expeditious, one-pot method for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones using a mixture of phosphorus pentoxide-methanesulfonic acid (Eaton’s reagent) at room temperature under solvent-free conditions is described. The salient features of this method include short reaction time, green aspects, high yields, and simple procedure.

scholarly journals Microwave Assisted One Pot Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives using [Emim]OH Ionic Liquid as Novel Catalyst

2019 ◽  
Vol 31 (4) ◽  
pp. 829-833
Author(s):  
D.S. Bhagat ◽  
S.G. Pande ◽  
M.V. Katariya ◽  
R.P. Pawar ◽  
P.S. Kendrekar
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
Aryl Aldehydes ◽  
Microwave Assisted ◽  
Novel Catalyst ◽  
Work Up

One-pot efficient protocol to the synthesis of 2-amino-5-oxo-4,5-dihydropyrano(3,2-c)chromene-3-carbonitrile derivatives via condensation of various aryl aldehydes, dicyanomethane and 4-hydroxycoumarin in presence of Emim hydroxide as an excellent homogeneous liquid catalyst. The key advantages of this methodology are mild reaction conditions, novel catalyst, short reaction time, eco-friendly, easy work-up procedure and high yield of isolation of derivatives.

scholarly journals Fe3O4@chitosan-tannic acid bionanocomposite as a novel nanocatalyst for the synthesis of pyranopyrazoles

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Maryam Kamalzare ◽  
Mohammad Reza Ahghari ◽  
Mohammad Bayat ◽  
Ali Maleki
Keyword(s):  
Reaction Time ◽  
Tannic Acid ◽  
High Performance ◽  
Catalytic Performance ◽  
Natural Material ◽  
Magnetic Nanocatalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
High Yields

AbstractRecently magnetic nanocatalyst has attracted considerable attention because of its unique properties, including high performance, easy separation from the reaction mixture, and recyclability. In this study, a novel magnetic bionanocomposite was synthesized with chitosan and tannic acid as a natural material. The synthesized bionanocatalyst was characterized by essential analysis. Fe3O4@chitosan-tannic acid as a heterogeneous nanocatalyst was successfully applied to synthesize pyranopyrazole and its derivatives by a one-pot four-component reaction of malononitrile, ethyl acetoacetate, hydrazine hydrate, and various aromatic aldehyde. At the end of the reaction, the nanocatalyst was separated from the reaction mixture and was reused several times with no significant decrease in its catalytic performance. Simple purification of products, the ability for recovering and reusing the nanocatalyst, eco-friendliness, high yields of pure products, mild reaction conditions, short reaction time, non-toxicity, economically affordable are some of the advantages of using the fabricated nanocatalyst in the synthesis of pyranopyrazole.

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.

scholarly journals Facile Synthesis of Spiro[cyclohexane-1,3’-indoline]-2,2’-diones

2019 ◽  
Vol 25 (1) ◽  
pp. 157-161 ◽  
Author(s):  
Shin-taro Katayama ◽  
Hiroshi Nishino
Keyword(s):  
Natural Products ◽  
Reaction Time ◽  
Total Synthesis ◽  
Facile Synthesis ◽  
One Pot ◽  
Short Reaction Time ◽  
High Yields

AbstractSpiro[cyclohexane-1,3’-indoline]-2,2’-diones were easily prepared in good to high yields by the oxidation of N-aryl-N-methyl-2-oxocyclohexane-1-carboxamides in one pot with a short reaction time. The spiroindolinediones could be important for the total synthesis of natural products.

scholarly journals Pentafluoropropionic Acid: An Efficient and Metal-Free Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
Naser Montazeri ◽  
Taghva Noghani ◽  
Mona Ghorchibeigy ◽  
Rozita Zoghi
Keyword(s):  
Reaction Time ◽  
Aromatic Aldehyde ◽  
One Pot ◽  
Short Reaction Time ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
The One ◽  
High Yields

Pentafluoropropionic acid (PFPA) efficiently catalyzes the one-pot, three-component reaction of aromatic aldehyde, malononitrile, and dimedone to yield tetrahydrobenzo[b]pyran derivatives in high yields. This method is of great value because of its easy processing, short reaction time, environmentally, and high yields.

Synthesis of a series of novel 2,3-dihydrofuranonaphthoquinone derivatives

2017 ◽  
Vol 41 (8) ◽  
pp. 448-451 ◽  
Author(s):  
Maryam Salari ◽  
Mohammad H. Mosslemin ◽  
Alireza Hassanabadi
Keyword(s):  
Reaction Time ◽  
Green Chemistry ◽  
Organic Solvent ◽  
Aromatic Aldehyde ◽  
Efficient Synthesis ◽  
One Pot ◽  
Short Reaction Time ◽  
Highly Efficient ◽  
One Pot Condensation ◽  
High Yields

A green and highly efficient synthesis of 12 novel trans-2-(4-chlorobenzoyl)-3-aryl-2,3-dihydronaphtho[2,3- b]furan-4,9-diones has been achieved via a three-component, one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 2-hydroxy-1,4-naphthoquinone and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water under reflux conditions. The advantages of this method are a short reaction time, high yields and the avoidance of any hazardous organic solvent. Therefore, this procedure can be classified as green chemistry.

Nucleophilic Acylation with Aromatic Aldehydes to 2 Bromoacetonitrile: An Umpolung Strategy for the Synthesis of Active Methylene Compounds

2020 ◽  
Vol 17 (7) ◽  
pp. 518-524
Author(s):  
Shailesh Singh ◽  
Jyoti Tiwari ◽  
Deepali Jaiswal ◽  
Amit Kumar Sharma ◽  
Jaya Singh ◽  
...  
Keyword(s):  
Reaction Time ◽  
Ambient Temperature ◽  
Aromatic Aldehydes ◽  
Product Formation ◽  
One Pot ◽  
Short Reaction Time ◽  
Salient Features ◽  
High Yields ◽  
Operational Simplicity ◽  
Nucleophilic Acylation

Background: A novel one-pot N-heterocyclic carbene (NHC)-catalysed acylation of 2- bromoacetonitrile with aromatic aldehydes is reported. The protocol involves carbonyl umpolung reactivity of aldehydes in which the carbonyl carbon attacks nucleophilically (as d1 nucleophile) on the electrophilic terminal of 2-bromoacetonitrile to afford 3-aryl-3-oxopropanenitrile. The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Materials and Methods: A flame-dried round bottom flask was charged with Imidazolium salts (3a) (0.20 mmol). Aldehyde 1a (1.0 mmol), 2-bromoacetonitrile 2 (1.0 mmol), and THF / t-BuOH 5 mL; 10:1) were added at positive nitrogen pressure followed by the addition of DBU (0.15 mmol) through stirring. The resulting yellow- orange solution was stirred at room temperature for 5-6 h. After completion of the reaction (TLC monitored), the reaction mixture was concentrated under reduced pressure. The product was purified using hexane / EtOAc (10:1) as an eluent to provide analytically pure compound 4a. Physical data of representative compounds and the NMR spectroscopic data are in agreement with the literature value. Results and Discussion: The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Conclusion: To sum up, we have developed a convenient, efficient and one-pot route for 3-oxo-3- phenylpropanenitrile synthesis from NHC promoted direct nucleophilic acylation of aromatic aldehydes using 2- bromoacetonitrile. This method provided a wide range of products and good yields. To best of our knowledge, this is the new report for the synthesis of 3-oxo-3-phenylpropanenitrile through NHC promoted nucleophilic acylation of aromatic aldehyde.

5-Pyrrolidin-2-yltetrazole-Promoted One-Pot Hantzsch Polyhydroquinoline Synthesis Using NH4HCO3 as Nitrogen Source

2008 ◽  
Vol 61 (11) ◽  
pp. 860 ◽  
Author(s):  
Weike Su ◽  
Jia Li ◽  
Jianjun Li
Keyword(s):  
Reaction Time ◽  
Coupling Reaction ◽  
Ammonium Bicarbonate ◽  
One Pot ◽  
Short Reaction Time ◽  
Environmental Friendly ◽  
Solvent Free Conditions ◽  
Active Methylene Compounds ◽  
High Yields ◽  
Active Methylene

A straightforward and green synthesis of polyhydroquinoline derivatives was reported via a four-component coupling reaction of aldehydes, dimedone, active methylene compounds, and ammonium bicarbonate in the presence of 5-pyrrolidin-2-yltetrazole under solvent-free conditions. The method offers several advantages including high yields, an environmental friendly procedure, a short reaction time, and easy isolation of products.

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.

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