A greener procedure for the synthesis of α-ureidophosphonates under ultrasound irradiation. An X-ray crystallographic study

RSC Advances ◽  
2015 ◽  
Vol 5 (121) ◽  
pp. 99775-99780 ◽  
Author(s):  
Abdeslem Bouzina ◽  
Malika Berredjem ◽  
Sofiane Bouacida ◽  
Hocine Merazig ◽  
Nour-eddine Aouf
Keyword(s):  
Ultrasonic Irradiation ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
One Pot ◽  
X Ray ◽  
Catalyst Free ◽  
Crystallographic Study ◽  
Three Component Reaction

The synthesis of α-ureidophosphonates via a one-pot three-component reaction using ultrasonic irradiation under solvent- and catalyst-free conditions at 75° is developed. The products were obtained in excellent yields within short reaction times.

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.

scholarly journals An Efficient, Clean, and Catalyst-Free Synthesis of Fused Pyrimidines Using Sonochemistry

2014 ◽  
Vol 2014 ◽  
pp. 1-9 ◽  
Author(s):  
M. Mamaghani ◽  
K. Tabatabaeian ◽  
R. Araghi ◽  
A. Fallah ◽  
R. Hossein Nia
Keyword(s):  
Ethylene Glycol ◽  
Ultrasonic Irradiation ◽  
Reaction Times ◽  
Quinoline Derivatives ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Catalyst Free ◽  
Three Component Reaction

In this report, synthesis of indenopyrido[2,3-d]pyrimidine and pyrimido[4,5-b]quinoline derivatives was investigated via one-pot three-component reaction between 6-amino-2-(alkylthio)-pyrimidin-4(3H)one, 1,3-indanedione, or 1,3-cyclohexadione and arylaldehyde under ultrasonic irradiation in ethylene glycol as solvent at 65°C. In these reactions fused pyrimidine derivatives were synthesized with high to excellent yields (82–97%) and short reaction times (10–33 min).

A one-pot three-component synthesis of novel α-sulfamidophosphonates under ultrasound irradiation and catalyst-free conditions

RSC Advances ◽  
2015 ◽  
Vol 5 (49) ◽  
pp. 39324-39329 ◽  
Author(s):  
Billel Belhani ◽  
Malika Berredjem ◽  
Marc Le Borgne ◽  
Zouhair Bouaziz ◽  
Jacques Lebreton ◽  
...  
Keyword(s):  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Solvent Free ◽  
One Pot ◽  
Mild Conditions ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
Work Up

A one-pot synthesis of novel α-sulfamidophosphonates is described via a three-component reaction under ultrasound irradiation, catalyst-free and solvent-free conditions. The synthesis has mild conditions, short reaction times, good yields and simple work-up procedures.

Catalyst-free, one-pot, four-component green synthesis of functionalized 1-(2-fluorophenyl)-1,4-dihydropyridines under ultrasound irradiation

2016 ◽  
Vol 40 (6) ◽  
pp. 5107-5112 ◽  
Author(s):  
Nhlanhla Shabalala ◽  
Suresh Maddila ◽  
Sreekantha B. Jonnalagadda
Keyword(s):  
Green Synthesis ◽  
Ultrasonic Irradiation ◽  
Aqueous Ethanol ◽  
Ultrasound Irradiation ◽  
One Pot ◽  
Catalyst Free ◽  
New Compounds ◽  
Synthesis Protocol

A catalyst-free synthesis protocol for functionalized 1,4-dihydropyridines under ultrasonic irradiation in aqueous ethanol is reported with excellent yields. Eleven new compounds are synthesized using dimethylacetylenedicarboxylate, 2-fluoroaniline, malononitrile and various substituted aldehydes.

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.

scholarly journals A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation

2020 ◽  
Vol 11 (3) ◽  
pp. 179-186
Author(s):  
Shunan Kaping ◽  
Philippe Helissey ◽  
Jai Narain Vishwakarma
Keyword(s):  
Aqueous Media ◽  
Ultrasound Irradiation ◽  
Mass Spectral Data ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Triclinic Space Group ◽  
X Ray ◽  
Mass Spectral ◽  
Chemical Structures ◽  
Crystallographic Study

A simple and efficient synthesis of substituted pyrazolo[1,5-a]pyrimidine derivatives has been developed by the use of ultrasound. 5-Methyl-4-phenyl-1H-pyrazol-3-amine required for the synthesis of pyrazolo[1,5-a]pyrimidine derivatives has been easily obtained by the reaction of 3-(dimethylamino)-2-phenylacrylonitrile (formed from readily available 2-phenylacetonitrile) with hydrazine hydrate in refluxing ethanol. The 5-aminopyrazole was then reacted with various formylated active proton compounds in presence of KHSO4 in aqueous medium under ultrasound irradiation to give the desired products. The chemical structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. X-ray crystallographic study of a selected compound 6-(4-chlorophenyl)-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine (7c) was performed to ascertain the regioselectivity of the reaction. Crystal data for compound 7c: Triclinic, space group P-1 (no. 2), a = 8.0198(3) Å, b = 14.0341(6) Å, c = 14.2099(6) Å, α = 87.672(2)°, β = 83.902(2)°, γ = 89.120(2)°, V = 1588.87(11) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.248 mm-1, Dcalc = 1.400 g/cm3, 12918 reflections measured (4.012° ≤ 2Θ ≤ 49°), 5152 unique (Rint = 0.0411, Rsigma = 0.0429) which were used in all calculations. The final R1 was 0.0486 (I > 2σ(I)) and wR2 was 0.1320 (all data).

Catalyst-Free Three-Component Synthesis of Spirobenzimidazolidines Bearing an Indole Scaffold

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2301-2305 ◽  
Author(s):  
F. Moghaddam ◽  
A. Moafi ◽  
Z. Zamani ◽  
M. Daneshfar
Keyword(s):  
Reaction Times ◽  
Reaction Conditions ◽  
One Pot ◽  
Efficient Catalyst ◽  
Catalyst Free ◽  
New Family ◽  
Three Component Reaction ◽  
High Yields ◽  
First Time ◽  
Derivatives Of

An efficient catalyst-free one-pot three-component reaction was developed for the synthesis of a new family of N- and S-containing spirocyclic compounds. Various derivatives of spirobenzimidazolidine containing an indole scaffold were synthesized for the first time in a modestly toxic solvent and under mild reaction conditions. The reaction times were of the order of several minutes, and all the products were obtained in moderate to high yields (overall yields 58–80%).

scholarly journals Fe3O4@urea/HITh-SO3H as an efficient and reusable catalyst for the solvent-free synthesis of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one and indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine derivatives

2020 ◽  
Vol 18 (1) ◽  
pp. 648-662
Author(s):  
Shenghao Jiang ◽  
Macheng Shen ◽  
Fatima Rashid Sheykhahmad
Keyword(s):  
Electron Microscopy ◽  
Reaction Times ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
Pyrimidine Derivatives ◽  
Magnetic Nanocatalyst ◽  
One Pot ◽  
X Ray ◽  
Solvent Free Conditions ◽  
Three Component Reaction

AbstractIn this study, Fe3O4@urea/HITh-SO3H MNPs as a new, efficient, and recyclable solid acid magnetic nanocatalyst was synthesized and characterized using various methods including Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, transmission electron microscopy, vibrating sample magnetometry, energy-dispersive X-ray spectroscopy, and X-ray powder diffraction. After the characterization of this new magnetic nanocatalyst, it was efficiently utilized for the promotion of the one-pot synthesis of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one and indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine derivatives via three-component reaction of the 1,3-indanedione, aldehyde, and 1-naphthylamine/1,3-dimethyl-6-aminouracil under solvent-free conditions at 80°C. The procedure gave the desired heterocyclic structures in high-to-excellent yields and short reaction times. Also because of the magnetic nature of the nanocatalyst, it can be separated with an external magnetic field and reused at least six runs without any considerable decrease in the catalytic behavior.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

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