Highly Efficient Ultrasound Promoted Synthesis of 2-phenylquinoxaline in Glycerol- Water

2020 ◽  
Vol 17 (6) ◽  
pp. 483-487
Author(s):  
Mujahed Shaikh ◽  
Devendra Wagare ◽  
Ashvini Sonone ◽  
Ayesha Durrani
Keyword(s):  
Medicinal Chemistry ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Organic Medium ◽  
Environmentally Benign ◽  
Green Method ◽  
One Pot ◽  
Glycerol Water ◽  
Highly Efficient ◽  
Volatile Organic

Introduction: Quinoxalines show diversified applications in the field of medicinal chemistry. Materials and Methods: Therefore, we have designed a highly efficient, environmentally benign and one-pot protocol for the synthesis of 2-phenylquinoxaline from the reaction of Acetophenone, N-bromosuccinimide and 1,2-phenylenediamine under ultrasound irradiation in glycerol-water. Results and Discussion: We observed that, although the reaction efficiently completed in all of these solvents, the use of glycerol-water with different ratios gives consistently higher yields (89–94%) and decreases reaction times. Conclusion: The main advantages of this protocol are that it is a green method, avoids the use of toxic catalysts and volatile organic medium and the product is obtained with excellent yield.

A highly efficient and green approach for the synthesis of pyrimido[4,5-b]quinolines using N,N-diethyl-N-sulfoethanaminium chloride

2021 ◽  
Vol 76 (2) ◽  
pp. 85-90
Author(s):  
Abdolkarim Zare ◽  
Manije Dianat
Keyword(s):  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Catalyst Amount ◽  
Green Protocol ◽  
Highly Efficient ◽  
Green Approach ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

Abstract A highly efficient and green protocol for the synthesis of pyrimido[4,5-b]quinolines has been described. The one-pot multicomponent reaction of dimedone with arylaldehydes and 6-amino-1,3-dimethyluracil in the presence of N,N-diethyl-N-sulfoethanaminium chloride ([Et3N–SO3H][Cl]) as an ionic liquid (IL) catalyst under solvent-free conditions afforded the mentioned compounds in high yields and short reaction times. Our protocol is superior to many of the reported protocols in terms of two or more of these factors: the reaction times, yields, conditions (solvent-free versus usage of organic solvents), temperature and catalyst amount.

Recent advance in ester synthesis by Multi Component Reactions (MCRs): A Review

2021 ◽  
Vol 25 ◽  
Author(s):  
Dhaval B. Patel ◽  
Jagruti A. Parmar ◽  
Siddharth S. Patel ◽  
Unnati J. Naik ◽  
Hitesh D. Patel
Keyword(s):  
Multicomponent Reactions ◽  
Medicinal Chemistry ◽  
Reaction Times ◽  
Synthetic Methods ◽  
Ester Synthesis ◽  
One Pot ◽  
Wide Range ◽  
Recent Developments ◽  
Ester Linkage ◽  
The One

: The synthesis of ester containing heterocyclic compounds via multicomponent reaction is one of the most preferable process in the synthetic organic chemistry and medicinal chemistry. Compounds containing ester linkage have a wide range of biological application in the pharmaceutical field. Therefore, many method have been developed for the synthesis of these type of derivatives. However, some of them are carried out in the presence of toxic solvents and catalysts, with lower yields, longer reaction times, low selectivities and by-products. Thus, the development of new synthetic methods for the ester synthesis is required in the medicinal chemistry. As we know, multicomponent reactions (MCRs) are a powerful tool towards the one-pot ester synthesis, so in this article we have reviewed the recent developments in ester synthesis. This work covers selected explanation of methods via multicomponent reactions to explore the methodological development in ester synthesis.

Ionic Liquid 4-(3-Methyl-1-imidazolio)-1-butanesulfonic Acid Hydrogen Sulfate-catalyzed Synthesis of Phthalazinetrione Derivatives

2012 ◽  
Vol 67 (7) ◽  
pp. 717-724
Author(s):  
Shihua Song ◽  
Xiang Deng ◽  
Zhi Guan ◽  
Yanhong He
Keyword(s):  
Ionic Liquid ◽  
Polyethylene Glycol ◽  
Condensation Reaction ◽  
Reaction Times ◽  
Solvent System ◽  
Environmentally Benign ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Simple Method ◽  
Peg 600

A simple method for the synthesis of phthalazinetrione derivatives by a one-pot three-component condensation reaction of phthalhydrazide, 1,3-dicarbonyl compounds and aldehydes catalyzed by the ionic liquid 4-(3-methyl-1-imidazolio)-1-butanesulfonic acid hydrogen sulfate ([BSO3HmIm]HSO4) is reported. Good to excellent yields were obtained in short reaction times in the solvent PEG 600 (polyethylene glycol 600) at 120 °C. The strategy proved to be efficient and environmentally benign. The catalyst/solvent system could easily be recovered and reused for at least 5 times without noticeable loss of activity

scholarly journals Hydrogen peroxide/dimethyl carbonate: a green system for epoxidation of N-alkylimines and N-sulfonylimines. One-pot synthesis of N-alkyloxaziridines from N-alkylamines and (hetero)aromatic aldehydes

2016 ◽  
Vol 18 (18) ◽  
pp. 4859-4864 ◽  
Author(s):  
Jamil Kraïem ◽  
Donia Ghedira ◽  
Thierry Ollevier
Keyword(s):  
Hydrogen Peroxide ◽  
Dimethyl Carbonate ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Green Method ◽  
One Pot ◽  
One Pot Synthesis ◽  
Green System

A green method for epoxidation of imines using an environmentally benign oxidant system, H2O2/dimethyl carbonate, was developed.

Nanofibre Sepiolite Catalyzed Green and Rapid Synthesis of 2-Amino-4H-chromene Derivatives

2018 ◽  
Vol 71 (1) ◽  
pp. 32 ◽  
Author(s):  
Arezou Mohammadinezhad ◽  
Batool Akhlaghinia
Keyword(s):  
Column Chromatography ◽  
Present Method ◽  
Simple Procedure ◽  
Reaction Times ◽  
Significant Decline ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Rapid Synthesis ◽  
One Pot ◽  
Highly Efficient

Nanofibre sepiolite catalyzed the rapid, clean, and highly efficient synthesis of 2-amino-4H-chromene derivatives by a one-pot, three-component condensation of a series of aldehydes, various enolizable C–H bonds (such as dimedone, α-naphthol, resorcinol, and 4-hydroxy-2H-chromen-2-one), and malononitrile in a mixture of water/ethanol. The present method offers several advantages such as high to excellent yields, short reaction times, mild reaction conditions, simple procedure, use of inexpensive, non-toxic, and naturally available catalyst, easy isolation of the products, and no need for column chromatography. The catalyst could be easily separated from the reaction mixture and can be reused for many consecutive trials without a significant decline in its reactivity.

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.

scholarly journals Ferrocene-Containing Ionic Liquid Supported on Silica Nanospheres (SiO2@Imid-Cl@Fc) as a Mild and Efficient Heterogeneous Catalyst for the Synthesis of Pyrano[3,2-b]Pyran Derivatives Under Ultrasound Irradiation

2018 ◽  
Vol 42 (1) ◽  
pp. 7-12 ◽  
Author(s):  
Reza Teimuri-Mofrad ◽  
Somayeh Esmati ◽  
Masoumeh Rabiei ◽  
Mahdi Gholamhosseini-Nazari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Ultrasound Irradiation ◽  
Xrd Analysis ◽  
Catalytic Performance ◽  
Significant Loss ◽  
One Pot ◽  
X Ray ◽  
Three Component Reaction

A novel heterogeneous silica nanosphere-supported ferrocene-containing ionic liquid catalyst (SiO2@Imid-Cl@Fc) was designed and synthesised and was systematically characterised by Fourier transform infrared (FTIR) spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) and X-ray diffraction (XRD) analysis. The catalytic activity of the SiO2@Imid-Cl@Fc catalyst was tested in a one-pot, three-component reaction of malononitrile and kojic acid with 15 aromatic aldehydes at room temperature under ultrasound irradiation. The products were pyrano[3,2-b]pyran derivatives, four of which are new. The catalyst exhibited good catalytic performance over short reaction times (15–20 min) and could be recycled at least five times without significant loss of activity.

Chemodivergent, multicomponent-tandem facile synthesis of novel 1H-pyrazolo[1,2-b]phthalazine-5,10-dione using acetic acid functionalized imidazolium salt {[cmdmim]I} as a recyclable catalyst

2019 ◽  
Vol 43 (21) ◽  
pp. 8266-8278 ◽  
Author(s):  
Parivash Jahanshahi ◽  
Manouchehr Mamaghani
Keyword(s):  
Acetic Acid ◽  
Acid Catalyst ◽  
Recyclable Catalyst ◽  
Environmentally Benign ◽  
Facile Synthesis ◽  
One Pot ◽  
Imidazolium Salt ◽  
Highly Efficient ◽  
Brønsted Acid Catalyst ◽  
Wide Range

A novel one-pot four-component, highly efficient and environmentally benign approach for the synthesis of a wide range of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives in the presence of acetic acid functionalized imidazolium salt as a newly synthesized Brønsted acid catalyst is described.

The Discovery of Ultrasound Irradiation as a Useful Tool for Accelerating Petasis Three-component Reaction: Synthesis of α-Arylglycines

2018 ◽  
Vol 15 (2) ◽  
pp. 256-266 ◽  
Author(s):  
Fan Yun ◽  
Chunhui Cheng ◽  
Jingxuan Li ◽  
Pingwah Tang ◽  
Qipeng Yuan
Keyword(s):  
Reaction Time ◽  
Glyoxylic Acid ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Secondary Amines ◽  
One Pot ◽  
Petasis Reaction ◽  
Three Component Reaction ◽  
Wide Range ◽  
High Yields

Aim and Objective: α-Arylglycines belong to an important class of non-proteinogenic amino acids. Petasis 3-component, one-pot reaction lends itself to be suitable for the synthesis of α-Arylglycines. Because of the low reactivity, Petasis reaction requires long reaction time. Our objective is to use ultrasound irradiation to accelerate this versatile Petasis' synthesis of α-Arylglycines. Materials and Methods: Ultrasound irradiation as a physical tool to accelerate the Petasis 3-component reaction without any auxiliary catalyst can significantly shorten the reaction time. The operation is simple. It can be applied to a wide range of substrates. In order to highlight the remarkable utility of the ultrasound in Petasis reaction, we have compared side-by-side the reactivity between the reaction with ultrasound and the one without ultrasound. Results: Using ultrasound, the reaction times of Petasis reactions with various amine substrates including primary and secondary amines, heterocyclic amines, with a wide variety of boronic acids having different substituents (activating and deactivating groups) in the phenyl rings, and with glyoxylic acid and salicylic aldehyde were shortened from 5 to more than 20-fold. Conclusion: We have discovered the first examples of an efficient ultrasound-promoted approach for Petasis reaction to prepare a series of α-arylglycines in high yields and in excellent purities. The low reactivity of the reactions in this study were significantly enhanced by the ultrasound irradiation. By virtue of the acceleration and the operational simplicity, the present ultrasound assisted Petasis reaction can find applications in the synthetic areas of the already widely used Petasis three-component reaction.

One-Pot Solvent-and Catalyst-Free Synthesis of Some New Heteroarylaminonaphthoquinones from Lawsone

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Nilufar Rahmani ◽  
Mahdieh Sadeghpour ◽  
Amir Mohamadi
Keyword(s):  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Heterocyclic Amines ◽  
Environmentally Benign ◽  
One Pot ◽  
Simple Operation ◽  
Catalyst Free ◽  
Three Component Reaction ◽  
Methyl Naphthalene ◽  
Work Up

: A clean and efficient one-pot protocol for the synthesis of a series of new 2-hydroxy-3-((3-aryl)(heteroarylamino)methyl)naphthalene-1,4-dione derivatives has been developed by the three-component reaction of 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and heterocyclic amines at 90 oC under solvent and catalyst-free conditions. The procedure avoids the use of toxic solvents, tedious work-up, catalyst and purification of the products by chromatographic methods. Simple operation, short reaction times, generating the desired compounds in high to excellent yields and an environmentally benign method are advantages of this protocol.

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