Ionic Liquid Catalyzed Efficient Regioselective Synthesis of 1,4- Disubstituted 1,2,3-Triazoles under Metal and Solvent free Conditions

2020 ◽  
Vol 07 ◽  
Author(s):  
Abid H. Banday ◽  
Victor J. Hruby
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Solvent Free ◽  
Regioselective Synthesis ◽  
Chromatographic Separations ◽  
One Pot ◽  
Green Protocol ◽  
Metal Free ◽  
Organic Azides ◽  
Solvent Free Conditions

Background: Unprecedented, one-pot regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles through azide- aldehyde (3+2) organo-click cycloaddition under metal and solvent-free conditions, is described. Objective: Solvent and metal free synthesis of biologically and industrially important triazoles. Methods: Efficient and high yielding synthesis of products avoiding the tedious high solvent workups and chromatographic separations. The synthesis doesn’t involve the routine acetylenes which are very costly but instead cheaper starting materials like aldehydes and organic azides are used. Results: Green protocol based on the catalysis through Ionic Liquids which simultaneously act as solvents. The products are obtained in good to excellent yields in hassle free synthesis. Conclusion: Efficient and green synthesis of structurally and biologically important triazoles.

scholarly journals Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

2018 ◽  
Vol 14 ◽  
pp. 2689-2697 ◽  
Author(s):  
Robby Vroemans ◽  
Yenthel Verhaegen ◽  
My Tran Thi Dieu ◽  
Wim Dehaen
Keyword(s):  
Multicomponent Reaction ◽  
Mechanochemical Synthesis ◽  
Solvent Free ◽  
Viable Alternative ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Biologically Relevant ◽  
Metal Free ◽  
Organic Azides ◽  
Solvent Free Conditions

A new metal-free one-pot three-component procedure towards fully substituted triazolochromenes has been developed, starting from commercially available materials. Salicylaldehydes and nitroalkenes were reacted under solvent-free conditions, followed by a 1,3-dipolar cycloaddition of the intermediate 3-nitro-2H-chromenes with organic azides in a one-pot two-step sequence. The triazolochromenes were formed with complete regioselectivity and new biologically relevant structures were synthesized via extension of the developed procedure and via postfunctionalization. The mechanochemical synthesis was carried out for several salicylaldehydes and gave a clear improvement in the yield of the corresponding triazolochromenes and consequently showed to be a viable alternative for solid salicylaldehydes.

1, 1’-Sulfinyldiethylammonium Bis (Hydrogen Sulfate) as a Recyclable Dicationic Ionic Liquid Catalyst for the Efficient Solvent-free Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction

2020 ◽  
Vol 23 (2) ◽  
pp. 157-167
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Dicationic Ionic Liquid

Objective: A facile and efficient method for synthesis of 3, 4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by a novel dicationic Brönsted acidic ionic liquid, [(EtNH2)2SO][HSO4]2, has been successfully developed. Material and Method:: 3, 4-Dihydropyrimidin-2(1H)-ones were synthesized through one-pot condensation of aromatic aldehydes, ethyl acetoacetate, and urea under solvent-free conditions using [(EtNH2)2SO][HSO4]2 as a novel catalyst. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate / n-hexane = 1 / 5). The products have been characterized by IR, 1H NMR, 13C NMR, and also by their melting points. Results: In this research, a library of dihydropyrimidinone derivatives was synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as a catalyst. Various aromatic aldehydes, as well as heteroaromatic aldehydes, were employed, affording good to high yields of the corresponding products and illustrating the substrate generality of the present method. In addition, the prepared dicationic Brönsted acidic ionic liquid can be easily recovered and reused. Conclusion: 1, 1’-Sulfinyldiethylammonium bis (hydrogen sulfate), as a novel dicationic ionic liquid, can act as a highly efficient catalyst for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions.

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.

An Efficient One-Pot Four-Component Hantzsch Reaction to Prepare Hydroquinolines Catalyzed by a Poly(ethylene glycol) Bridged Dicationic Basic Ionic Liquid under Solvent-Free Conditions

2013 ◽  
Vol 781-784 ◽  
pp. 247-252
Author(s):  
Jun Luo ◽  
Tan Tan Xing ◽  
Ying Lei Wang ◽  
Jian Feng Ju
Keyword(s):  
Ionic Liquid ◽  
Ethylene Glycol ◽  
Solvent Free ◽  
Hantzsch Reaction ◽  
Poly Ethylene Glycol ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Basic Ionic Liquid ◽  
Activity Loss ◽  
Poly Ethylene

A piperidine-functionalized poly (ethylene glycol) bridged dicationic ionic liquid PEG800-DPIL(Cl) was synthesized and applied to catalyze the four-component Hantzsch reaction under solvent-free conditions and afford hydroquinolines with high to excellent yields. PEG800-DPIL(Cl) could be recovered by simple workup and recycled for at least eight times without obvious activity loss.

A straightforward one-pot synthesis of bioactive N-aryl oxazolidin-2-ones via a highly efficient Fe3O4@SiO2-supported acetate-based butylimidazolium ionic liquid nanocatalyst under metal- and solvent-free conditions

2017 ◽  
Vol 19 (16) ◽  
pp. 3801-3812 ◽  
Author(s):  
Radhika Gupta ◽  
Manavi Yadav ◽  
Rashmi Gaur ◽  
Gunjan Arora ◽  
Rakesh Kumar Sharma
Keyword(s):  
Ionic Liquid ◽  
Solvent Free ◽  
Magnetic Nanocatalyst ◽  
One Pot ◽  
Supported Ionic Liquid ◽  
Highly Efficient ◽  
One Pot Synthesis ◽  
Solvent Free Conditions

A supported ionic liquid-based magnetic nanocatalyst has been fabricated for the formation of pharmaceutically important N-aryl oxazolidin-2-ones.

A facile and highly convergent approach to thiazolo[3,2-a]pyridines via one-pot multicomponent domino reaction under metal-free and solvent-free conditions

Tetrahedron ◽  
2015 ◽  
Vol 71 (21) ◽  
pp. 3422-3427 ◽  
Author(s):  
Anugula Nagaraju ◽  
B. Janaki Ramulu ◽  
Gaurav Shukla ◽  
Abhijeet Srivastava ◽  
Girijesh Kumar Verma ◽  
...  
Keyword(s):  
Solvent Free ◽  
Domino Reaction ◽  
One Pot ◽  
Metal Free ◽  
Solvent Free Conditions ◽  
Convergent Approach
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