One-Pot Catalytic Epoxidation Reaction of Perfluoro-2-methyl-2-pentene with Tri-n-butylamine N-Oxide or N, N-Dimethylcyclohexylamine N-Oxide

2013 ◽  
Vol 685 ◽  
pp. 357-361 ◽  
Author(s):  
Min Sha ◽  
Ren Ming Pan ◽  
Biao Jiang
Keyword(s):  
Organic Chemistry ◽  
Hydrogen Peroxide ◽  
Low Cost ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalytic Epoxidation ◽  
Epoxidation Reaction ◽  
Work Up ◽  
Better Than

Perfluoro epoxy compounds are important intermediates in organic chemistry, however, the methods for preparing them are scanty. We found that in situ generated tri-n-butylamine N-oxide and N,N-Dimethylcyclohexylamine N-oxide were found to be good reagents for the epoxidation of tri-substituted Perfluoro-2-methyl-2-pentene in good to excellent yields. Catalytic epoxidation methods were developed by coupling this reaction with the N-oxidation of tertiary amine by hydrogen peroxide or MCPBA. The advantages of these methods are easy work-up, mild reaction conditions, environmentally friendly and low cost. The reaction using MCPBA as a oxidant is better than hydrogen peroxide for it is fast and high yielding.

scholarly journals Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

2018 ◽  
Vol 14 ◽  
pp. 1655-1659 ◽  
Author(s):  
Ugo Azzena ◽  
Massimo Carraro ◽  
Gloria Modugno ◽  
Luisa Pisano ◽  
Luigi Urtis
Keyword(s):  
Organic Chemistry ◽  
Heterogeneous Catalysis ◽  
Important Class ◽  
Green Solvents ◽  
Reaction Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Acidic Catalysts ◽  
Set Up ◽  
Work Up

The application of heterogeneous catalysis and green solvents to the set up of widely employed reactions is a challenge in contemporary organic chemistry. We applied such an approach to the synthesis and further conversion of tetrahydropyranyl ethers, an important class of compounds widely employed in multistep syntheses. Several alcohols and phenols were almost quantitatively converted into the corresponding tetrahydropyranyl ethers in cyclopentyl methyl ether or 2-methyltetrahydrofuran employing NH4HSO4 supported on SiO2 as a recyclable acidic catalyst. Easy work up of the reaction mixtures and the versatility of the solvents allowed further conversion of the reaction products under one-pot reaction conditions.

Epoxidation of Olefins Catalyzed by Polyoxomolybdates Formed in-situ in Ionic Liquids

2013 ◽  
Vol 68 (10) ◽  
pp. 1138-1142 ◽  
Author(s):  
Lilian R. Graser ◽  
Sophie Jürgens ◽  
Michael E. Wilhelm ◽  
Mirza Cokoja ◽  
Wolfgang A. Herrmann ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Hydrogen Peroxide ◽  
Ionic Liquid ◽  
Catalyst Concentration ◽  
Sodium Molybdate ◽  
Significant Loss ◽  
Catalytic Epoxidation ◽  
Epoxidation Reaction ◽  
Epoxidation Of Olefins

Polyoxomolybdates were generated in situ by treating a carboxylic acid-functionalized ionic liquid with an aqueous solution of sodium molybdate. This reaction mixture was applied in the catalytic epoxidation of olefins using hydrogen peroxide as oxidant. The influence of acid and catalyst concentration as well as of the reaction temperature was investigated. The system showed a good performance for the epoxidation reaction and can be reused several times without a significant loss of activity. We present an easy, cheap and environmentally friendly catalytic system for the epoxidation of cis-cyclooctene.

scholarly journals One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1466
Author(s):  
Ye Eun Kim ◽  
Hyunsung Cho ◽  
Yoo Jin Lim ◽  
Chorong Kim ◽  
Sang Hyup Lee
Keyword(s):  
Alkyl Halide ◽  
The Novel ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Consecutive Reactions ◽  
Intramolecular Condensation ◽  
Synthetic Sequence ◽  
Novel Target

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2·2H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1–2 h at 40 °C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1–4 h at 25–50 °C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.

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.

An efficient multicomponent, one-pot synthesis of Betti bases catalyzed by cerium (IV) ammonium nitrate (CAN) at ambient temperature

2016 ◽  
Vol 5 (4) ◽  
Author(s):  
Ramadan Ahmed Mekheimer ◽  
Abdullah Mohamed Asiri ◽  
Afaf Mohamed Abdel Hameed ◽  
Reham R. Awed ◽  
Kamal Usef Sadek
Keyword(s):  
Ambient Temperature ◽  
Environmental Pollution ◽  
Ammonium Nitrate ◽  
Room Temperature ◽  
Catalytic Amount ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Work Up ◽  
Cerium Iv Ammonium Nitrate

AbstractStarting from readily available 2-naphthol, aldehydes, aryl and alkylamines, a variety of Betti bases were efficiently synthesized utilizing a catalytic amount of cerium (IV) ammonium nitrate (CAN) at room temperature. This protocol has advantages of high yield, mild reaction conditions, no environmental pollution, diversity of reactants and simple work up procedure.

scholarly journals Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

2013 ◽  
Vol 9 ◽  
pp. 974-982 ◽  
Author(s):  
Tamashree Ghosh ◽  
Abhishek Santra ◽  
Anup Kumar Misra
Keyword(s):  
Reaction Sequence ◽  
Reaction Conditions ◽  
One Pot ◽  
Carbon Tetrabromide

A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good.

scholarly journals Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

2013 ◽  
Vol 9 ◽  
pp. 2344-2353 ◽  
Author(s):  
Sudipta Pathak ◽  
Kamalesh Debnath ◽  
Animesh Pramanik
Keyword(s):  
Sulfuric Acid ◽  
Low Cost ◽  
Solvent Free ◽  
Primary Amines ◽  
Solid Catalyst ◽  
Silica Sulfuric Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Solvent Free Reaction

A convenient and efficient methodology for the synthesis of densely substituted pyrrole-fused isocoumarins, which employs solid-supported silica sulfuric acid (SSA) as catalyst, has been developed. When the mixture of ninhydrin adducts of acetylacetone/ethyl acetoacetate and primary amines was heated on the solid surface of SSA under solvent-free conditions, the pyrrole-fused isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the starting materials, and the excellent yields of products.

scholarly journals A novel Pd-catalysed sequential carbonylation/cyclization approach toward bis- N -heterocycles: rationalization by electronic structure calculations

2018 ◽  
Vol 5 (9) ◽  
pp. 181140 ◽  
Author(s):  
Liliana Damas ◽  
Rui M. B. Carrilho ◽  
Sandra C. C. Nunes ◽  
Alberto A. C. C. Pais ◽  
László Kollár ◽  
...  
Keyword(s):  
Electronic Structure ◽  
Electronic Structure Calculations ◽  
Reaction Conditions ◽  
One Pot ◽  
New Family ◽  
Synthetic Strategy ◽  
Heterocyclic Derivatives ◽  
Amine Groups ◽  
Structure Calculations

An unprecedented palladium-catalysed sequential aminocarbonylation/cyclization synthetic strategy, using carbon monoxide and structurally different aliphatic diamines as N -nucleophiles, gives access, in one pot, to a new family of indole-based N -heterocyclic derivatives (hydropyrazinones, benzodiazepinones and hydroquinoxalines). Optimization of the reaction conditions towards double carbonylation ( P CO = 30 bar, T = 80°C, iodoindole/diamine ratio = 1 : 1.5, toluene as solvent) allowed the target cyclic products, which are formed in situ via intramolecular cyclization of the ketocarboxamide intermediates, to be obtained through a nucleophilic addition/elimination reaction with the pendant terminal amine groups. The structure of the diamine nucleophile was revealed to affect the reaction's selectivity, with the best yields for the cyclic products being obtained in the presence of (1 S , 2S )-(+)-cyclohexane-1,2-diamine ( a ) as the nucleophile, using either 5- or 7-iodoindole as the substrate. The reaction's selectivity was rationalized based on electronic structure calculations, which explain the effect of the diamine structure on the predominant formation of the cyclic products.

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