A solvent-free protocol for facile condensation of indoles with carbonyl compounds using silica chloride as a new, highly efficient, and mild catalyst

2007 ◽  
Vol 85 (6) ◽  
pp. 416-420 ◽  
Author(s):  
Alireza Hasaninejad ◽  
Abdolkarim Zare ◽  
Hashem Sharghi ◽  
Mohsen Shekouhy ◽  
Reza Khalifeh ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Electrophilic Substitution ◽  
Room Temperature ◽  
Low Cost ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Solvent Free ◽  
Substitution Reactions ◽  
Aldehydes And Ketones ◽  
High Yields

A simple and efficient solvent-free procedure for the preparation of bis(indolyl)methanes via electrophilic substitution reactions of indoles with aldehydes and ketones is described. The reactions took place in the presence of a catalytic amount of silica chloride at room temperature. The advantages of this method are high yields, short reaction times, low cost, and compliance with green-chemistry protocols.Key words: silica chloride, indole, carbonyl compound, solvent-free, bis(indolyl)methane.

scholarly journals P2O5/SiO2as a New, Efficient and Reusable Catalyst for Preparation of 4,4′-Epoxydicoumarins Under Solvent-free Conditions

2011 ◽  
Vol 8 (4) ◽  
pp. 1626-1631 ◽  
Author(s):  
Liqiang Wu ◽  
Xiao Wang
Keyword(s):  
Silica Gel ◽  
Low Cost ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Phosphorus Pentoxide ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
Solvent Free Conditions ◽  
High Yields

An efficient solvent-free procedure for the preparation of 4,4′-epoxydicoumarins via the ondensation of 4-hydroxycoumarin with aldehydes in the presence of catalytic amount of phosphorus pentoxide/silica gel at 110°C is described. The advantages of this method are generality, high yields, short reaction times, ease of product isolation, low cost and ecologically friendly.

A Facile and Efficient Conversion of Aldehydes into 1,1-Diacetates (Acylals) using Iron(III) Fluoride as a Novel Catalyst

2007 ◽  
Vol 60 (8) ◽  
pp. 590 ◽  
Author(s):  
V. T. Kamble ◽  
R. A. Tayade ◽  
B. S. Davane ◽  
K. R. Kadam
Keyword(s):  
Large Scale ◽  
Room Temperature ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Solvent Free ◽  
Present System ◽  
Efficient Conversion ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Novel Catalyst

Aldehydes are smoothly converted into the corresponding 1,1-diacetates (acylals) in high yields in the presence of a catalytic amount (0.1 mol-%) of iron(III) fluoride at room temperature. The noteworthy features of the present system are shorter reaction times, chemoselective protection of aldehydes, and solvent-free conditions. The procedure is especially useful for large-scale syntheses as the catalyst is highly effective from the view of activity, selectivity, reusability, and economy in the preparation of 1,1-diacetates (acylals).

Electrophilic Substitution Reactions of Indoles with Carbonyl Compounds Using Ceric Ammonium Nitrate: A Novel and Efficient Method for the Synthesis of Di- and Tri-Indolylmethanes1

2003 ◽  
Vol 2003 (2) ◽  
pp. 72-74 ◽  
Author(s):  
C. Ramesh ◽  
N. Ravindranath ◽  
Biswanath Das
Keyword(s):  
Ammonium Nitrate ◽  
Efficient Method ◽  
Carbonyl Compounds ◽  
Electrophilic Substitution ◽  
Room Temperature ◽  
Ceric Ammonium Nitrate ◽  
Substitution Reactions ◽  
Electrophilic Substitution Reactions ◽  
High Yields

Ceric ammonium nitrate (CAN) is used to catalyse the electrophilic substitution reactions of indoles with carbonyl compounds at room temperature to produce di- and tri-indolylmethanes in high yields.

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

scholarly journals Polystyrene-supported aluminum chloride as an efficient and reusable catalyst for condensation of indole with various carbonyl compounds

2010 ◽  
Vol 75 (4) ◽  
pp. 423-431 ◽  
Author(s):  
Bahman Tamami ◽  
Nasrolahi Shirazi ◽  
Parvanak Borujeni
Keyword(s):  
Aluminum Chloride ◽  
Carbonyl Compounds ◽  
Low Cost ◽  
Reaction Times ◽  
Reusable Catalyst ◽  
Reaction Conditions ◽  
Crosslinked Polystyrene ◽  
Aldehydes And Ketones ◽  
Polymeric Catalyst ◽  
Work Up

Crosslinked polystyrene-supported aluminum chloride (Ps-AlCl3) is a stable, recyclable and environmental friendly heterogeneous catalyst for the condensation of indole with aldehydes and ketones to afford bis-indolylmethanes. In addition, (Ps-AlCl3) shows satisfactory selectivity in the reaction of mixtures of an aldehyde and a ketone with indole. Although AlCl3 is a water sensitive, corrosive and environmentally harmful compound, Ps-AlCl3 is a stable and water-tolerant species. The mild reaction conditions, short reaction times, easy work-up, high to excellent yields, chemoselectivity, reuse of the catalyst for at least ten times without significant change in its catalytic activity, low cost, and easy preparation and handling of the polymeric catalyst are obvious advantages of the present method.

scholarly journals LEUCINE : AN EFFICIENT AND GREEN AMINO ACID CATALYST FOR CONVERSION OF ALDEHYDES AND KETONES INTO GEM-DIHYDROPEROXIDES WITH H2O2

2016 ◽  
Vol 11 (2) ◽  
pp. 3452-3458 ◽  
Author(s):  
Davood Azarifar ◽  
Ommolbanin Badalkhani ◽  
Kaveh Khosravi ◽  
Younes Abbasi
Keyword(s):  
Amino Acid ◽  
Present Method ◽  
Room Temperature ◽  
Reaction Times ◽  
Acid Catalyst ◽  
Aqueous Hydrogen Peroxide ◽  
Reaction Conditions ◽  
Green Catalyst ◽  
Aldehydes And Ketones ◽  
High Yields

Leucine amino acid, has been explored as an effective catalyst for conversion of ketones and aldehydes into corresponding gem-dihydroperoxides using 30% aqueous hydrogen peroxide in acetonitrile at room temperature. The reactions proceed smoothly within short periods of time to provide the respective gem-dihydroperoxides in excellent yields. Mild reaction conditions, low reaction times, high yields, low environmental impact, use of non-expensive, recyclable and green catalyst are the main merits of the present method.

Direct benzylation of 1,3-dicarbonyl compounds catalyzed by Cs2.5H0.5PW12O40 in solvent-free conditions

2011 ◽  
Vol 89 (12) ◽  
pp. 1533-1538 ◽  
Author(s):  
Ezzat Rafiee ◽  
Maryam Khodayari ◽  
Mohammad Joshaghani
Keyword(s):  
Carbonyl Compounds ◽  
Reaction Times ◽  
Solvent Free ◽  
Dicarbonyl Compounds ◽  
Environmentally Conscious ◽  
Benzylic Alcohols ◽  
Solvent Free Conditions ◽  
Excellent Activity ◽  
High Yields ◽  
Reaction Profile

Various 1,3-dicarbonyl compounds reacted readily with benzylic alcohols in the presence of Cs2.5H0.5PW12O40 salt to produce 2-benzylic-1,3-dicarbonyl compounds in high yields. It was found that this catalyst could be completely recovered and reused without loss of its catalytic activities and is thus environmentally conscious especially in solvent-free conditions. The use of this method provides improved modification of the direct benzylation of 1,3-carbonyl compounds in terms of low reaction times, solvent-free conditions, usage of a small amount of the catalyst, and a clean reaction profile. Furthermore, the use of this catalyst is feasible because of its easy preparation, its easy handling, its stability, its easy recovery, its reusability, being environmentally green, its excellent activity, and its selectivity.

Telluration of Alkenylmethyl Ketones with Aryltellurium Trichlorides: Synthetic Route and Structural Studies

2018 ◽  
Vol 2 (01) ◽  
Author(s):  
Mariya Khan ◽  
Ashok K. S. Chauhan ◽  
Ramesh C. Srivastava ◽  
Andrew Duthie ◽  
R. J. Butcher
Keyword(s):  
Carbonyl Compounds ◽  
Electrophilic Substitution ◽  
Room Temperature ◽  
Structural Studies ◽  
X Ray Diffraction ◽  
Substitution Reactions ◽  
X Ray ◽  
Work Up ◽  
Organotellurium Compounds ◽  
Moderate Yield

It has been our endeavor to prepare organotellurium compounds bearing functionalized groups. The electrophilic substitution reactions were performed with 1-acetyl-1-cyclohexene, an alkenylmethyl ketone (cyclo-C6H9COCH3), with NpTeCl3 and MesTeCl3. The reactions were found to proceed smoothly at room temperature. The unsymmetrical functionalized arylalkyltellurium dichloride Np(cyclo-C6H9COCH2)TeCl2, 1Aa or Mes(cyclo-C6H9COCH2)TeCl2, 1Ba was obtained in good to moderate yield when the reactants were stirred for 7-8 h in absence of any solvent. The reaction with MesTeCl3 is rather slow and requires over 24 h of stirring. Biphasic (H2O/CH2Cl2) reduction of the dichlorides 1Aa or 1Ba with aqueous Na2S2O5 did not gave the expected unsymmetrical telluroether (cyclo-C6H9COCH2)-Te-Ar, instead the usual work up of the organic phase afforded the respective ditellurides, Ar2Te2. The bromo analogues of 1Aa and 1Ba, namely Ar(cyclo-C6H9COCH2)TeBr2 (Ar= 1-Np, 1Ab and Mes, 1Bb), were prepared by the metathetical reaction of the chlorides with sodium bromide (Scheme 1). The newly synthesized dihaloaryltellurated alkenyl carbonyl compounds are colourless to pale yellow crystalline solids soluble in common organic solvents and have been characterized by 1H, 13C and 125Te NMR in solution. The structural studies in the solid state for the compounds 1Aa and 1Ba have been carried out by single-crystal X-ray diffraction technique

Green Protocol for Synthesis of Bis-indolylmethanes and Bis-indolylglycoconjugates in the Presence of Iron(III) Fluoride as a Heterogeneous, Reusable, and Eco-Friendly Catalyst

2006 ◽  
Vol 59 (11) ◽  
pp. 837 ◽  
Author(s):  
Vinod T. Kamble ◽  
Babasaheb P. Bandgar ◽  
Satish B. Suryawanshi ◽  
Sudhir N. Bavikar
Keyword(s):  
Efficient Method ◽  
Carbonyl Compounds ◽  
Catalytic Amount ◽  
Solvent Free ◽  
Environmentally Benign ◽  
Good Activity ◽  
Green Protocol ◽  
Solvent Free Conditions ◽  
High Yields

An efficient method for the preparation of bis-indolylmethanes and bis-indolylglycoconjugates from carbonyl compounds with indoles in the presence of a catalytic amount of iron(iii) fluoride under solvent-free conditions is reported. The desired products were obtained in high yields with a simple and environmentally benign procedure. The use of iron(iii) fluoride is feasible because of its stability, easy handling, easy recovery, reusability, and good activity.

Preparation and Characterization of a Novel Room Temperature Dicationic Ionic Liquid and its Application in the Synthesis of Xanthenediones Under Solvent-Free Conditions

2018 ◽  
Vol 21 (8) ◽  
pp. 602-608 ◽  
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Reaction Times ◽  
Significant Loss ◽  
Solvent Free ◽  
Acidity Function ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Hammett Acidity Function ◽  
Dicationic Ionic Liquid

Aim and Objective: In the present work, 1, 1’-sulfinyldiethylammonium bis (hydrogen sulfate) as a novel room temperature dicationic ionic liquid was synthesized and used as a catalyst for xanthenediones synthesis. Material and Method: The dicationic ionic liquid has been synthesized using ethylamine and thionyl chloride as precursors. Then, by the reaction of [(EtNH2)2SO]Cl2 with H2SO4, [(EtNH2)2SO][HSO4]2 was prepared and after that, it was characterized by FT-IR, 1H NMR, 13C NMR as well as Hammett acidity function. This dicationic ionic liquid was used as a catalyst for the synthesis of xanthenediones via condensation of structurally diverse aldehydes and dimedone under solvent-free conditions. The progress of the reaction was monitored by thin layer chromatography (ethyl acetate/n-hexane = 3/7). Results: An efficient solvent-free method for the synthesis of xanthenediones has been developed in the presence of [(EtNH2)2SO][HSO4]2 as a powerful catalyst with high to excellent yields, and short reaction times. Additionally, recycling studies have demonstrated that the dicationic ionic liquid can be readily recovered and reused at least four times without significant loss of its catalytic activity. Conclusion: This new dicationic ionic liquid can act as a highly efficient catalyst for xanthenediones synthesis under solvent-free conditions.

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