Green synthesis of 1H-pyrazolo[1,2-b]phthalazinedione-2-carbonitriles in the presence of L-proline

2021 ◽  
Vol 08 ◽  
Author(s):  
Davood Habibi ◽  
Saeedeh Shojaei ◽  
Somayyeh Heydari
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Green Synthesis ◽  
Organic Materials ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Diverse Range ◽  
Three Component Reaction ◽  
The One ◽  
Green Conditions

Background: The multi component reaction (MCRs) is a method extensively used in organic chemistry as a tool in the synthesis of nitrogen containing heterocycles found in many natural products, medicinally relevant substances and organic materials. Objective: This paper describes the synthesis of a diverse range of 1H-pyrazolo[1,2-b]phthalazine-2-carbonitriles of considerable chemical and biological interests. Conclusion: Various 3-amino-5,10-dioxo-1-phenyl-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbo -nitriles were synthesized via the one-pot three component reaction of phthalhydrazides, aromatic aldehydes and malononitrile in the presence of the proline as an organocatalyst in ethanol at refluxing temperature under the green conditions in excellent yields.

CeCl3·7H2O as mild and efficient catalyst for the one-pot multicomponent synthesis of 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones

2011 ◽  
Vol 76 (4) ◽  
pp. 235-241 ◽  
Author(s):  
Li-Qiang Wu ◽  
Wei-Lin Li ◽  
Fu-Lin Yan
Keyword(s):  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Work Up

A series of new 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones were synthesized via a three-component reaction of 3,4-methylenedioxyphenol, aromatic aldehydes and Meldrum’s acid in the presence of CeCl3·7H2O under solvent-free conditions. The method provided several advantages such as easy work-up, high yields and environmentally benign procedure.

Green Synthesis of 4-aryl-3,4-Dihydrochromeno[3,4-e][1,3]Oxazine-2,5-Dione in Aqueous Media by Condensation of 4-Hydroxycoumarin with Aromatic Aldehydes and Methyl Carbamate

2017 ◽  
Vol 41 (3) ◽  
pp. 136-138 ◽  
Author(s):  
Sabereh Bougan ◽  
Alireza Hassanabadi
Keyword(s):  
Green Chemistry ◽  
Organic Solvent ◽  
Green Synthesis ◽  
Aqueous Media ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Efficient Synthesis ◽  
One Pot ◽  
Three Component Reaction ◽  
High Yields

A green and efficient synthesis of the title compounds has been achieved in a one-pot, three-component reaction of 4-hydroxycoumarin and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones in excellent yields. The salient features of this protocol are: short reaction times, high yields and absence of any hazardous organic solvent. Consequently, this procedure could be classified as green chemistry.

Reactions Involving Aryl Methyl Ketone and Molecular Iodine: A Powerful Tool in the One-Pot Synthesis of Heterocycles

2021 ◽  
Author(s):  
Saideh Rajai-Daryasarei ◽  
Mohammad Hossein Gohari ◽  
Narges Mohammadi
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Heterocyclic Compounds ◽  
Methyl Ketone ◽  
Molecular Iodine ◽  
Bioactive Molecules ◽  
One Pot ◽  
Material Sciences ◽  
The One ◽  
Aryl Methyl

The preparation of heterocyclic compounds has attracted great attention in organic chemistry because of their extensive presence in bioactive molecules, material sciences, and natural products. Accordingly, the straightforward design and...

One-pot synthesis of 1-(benzothiazolylamino)aryl methyl-2-naphthols and 3-benzothiazolyl 2,3-dihydroquinazolinones using a magnetically recoverable core–shell nanocomposite as catalyst

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Yousef Mardani ◽  
Zahed Karimi-Jaberi ◽  
Mohammad Jaafar Soltanian Fard
Keyword(s):  
Reaction Times ◽  
Chemical Waste ◽  
One Pot ◽  
Significant Deterioration ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Green Conditions ◽  
Aryl Methyl ◽  
Operational Simplicity

Abstract Nano-magnetite-supported sulfated polyethylene glycol (Fe3O4@PEG-SO3H) was prepared, characterized and utilized as a magnetically recoverable heterogeneous catalyst for the one-pot, three-component reaction of 2-aminobenzothiazole, aldehydes and 2-naphthol/isatoic anhydride resulting in efficient formation of 1-(benzothiazolylamino)arylmethyl-2-naphthol or dihydroquinazolinones derivatives. The significant features of this method include green conditions, operational simplicity, minimizing production of chemical waste, shorter reaction times and good to high yields. In addition, the nanocatalyst can easily be separated from the reaction mixture by application of a magnetic field and reused without significant deterioration in its catalytic activity.

Development of N,N-disulfo-1,1,3,3-tetramethylguanidinium chlorometallates as heterogeneous catalysts for one pot synthesis of 1,2-dihydro-1-aryl-3H-naphth[1, 2-e][1,3]oxazin-3-one derivatives

2020 ◽  
Vol 07 ◽  
Author(s):  
Arup Kumar Dutta ◽  
Ruli Borah ◽  
Kabita Boruah
Keyword(s):  
Heterogeneous Catalysts ◽  
Analytical Techniques ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Metal Chlorides ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
The One ◽  
Acidic Compounds ◽  
Recyclable Heterogeneous Catalyst

Background: Four members of N,N-disulfo-1,1,3,3-tetramethylguanidinium chlorometallates [DSTMG]n[X], where n= 1 or 2; X= FeCl4 - , Zn2Cl6 2-, NiCl4 2-, MnCl4 2- were synthesized as solid Brønsted-Lewis acidic compounds and studied the catalytic activity with the most acidic salt for three-component synthesis of 1,2-dihydro-1-aryl-3H-naphth[1,2- e][1,3]oxazin-3-ones. Methods: N,N-disulfo-1,1,3,3-tetramethylguanidinium chlorometallates of the four transition metal cations such as Fe(III), Zn(II), Ni(II) and Mn(II) were prepared after treatment of the parent ionic liquid N,N-disulfo-1,1,3,3- tetramethylguanidinium chloride [DSTMG][Cl] with the respective metal chlorides in different mole fractions at 75 ºC. The synthesis of 1,2-dihydro-1-aryl-3H-naphth[1,2-e][1,3]oxazin-3-ones was carried out via three-component reaction of 2-naphthol, aromatic aldehydes and urea under neat condition at 90 ºC using 7 mol% of the [DSTMG][FeCl4] catalyst. Results: The characterization of synthesized chlorometallates were done using spectroscopic and other analytical techniques including thermogravimetric analysis and Hammett acidity studies. Among the four salts, the salt of Fe(III) ion was observed as the strong Brønsted acidic hydrophobic salt and thus chosen for the catalytic study. Conclusion: A new type of chlorometallates of guanidinium cation with composition [DSTMG]n[X], where X= FeCl4 - /Zn2Cl6 2-/ NiCl4 2-/ MnCl4 2- and n= 1 or 2 were developed as –SO3H functionalized solid acids with varied thermal stability (150-250 ºC) and physisorbed water (0-20%) as observed from the thermogravimetric study. From them, the most Brønsted acidic Fe(III) salt was employed as efficient recyclable heterogeneous catalyst for the one-pot synthesis of 1,2- dihydro-1-aryl-3H-naphth[1,2-e][1,3]oxazin-3-ones in neat condition.

Al(H2PO4)3 as an efficient and recyclable catalyst for the one-pot synthesis of naphthopyranopyrimidines

RSC Advances ◽  
2015 ◽  
Vol 5 (36) ◽  
pp. 28038-28043 ◽  
Author(s):  
Seyed Sajad Sajadikhah
Keyword(s):  
Aromatic Aldehydes ◽  
Recyclable Catalyst ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
The One

An efficient one-pot protocol has been developed for the synthesis of naphthopyranopyrimidine derivatives via a three-component reaction of aromatic aldehydes, β-naphthol and 6-amino-1,3-dimethyl uracil in the presence of Al(H2PO4)3.

Synthesis and Kinetics of Highly Substituted Piperidines in the Presence of Tartaric Acid as a Catalyst

2018 ◽  
Vol 21 (4) ◽  
pp. 302-311
Author(s):  
Younes Ghalandarzehi ◽  
Mehdi Shahraki ◽  
Sayyed M. Habibi-Khorassani
Keyword(s):  
Ambient Temperature ◽  
Tartaric Acid ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Rate Determining Step ◽  
State Approximation ◽  
Solvent Free Conditions ◽  
Steady State Approximation ◽  
Absorbance Changes ◽  
The One

Aim & Scope: The synthesis of highly substituted piperidine from the one-pot reaction between aromatic aldehydes, anilines and β-ketoesters in the presence of tartaric acid as a catalyst has been investigated in both methanol and ethanol media at ambient temperature. Different conditions of temperature and solvent were employed for calculating the thermodynamic parameters and obtaining an experimental approach to the kinetics and mechanism. Experiments were carried out under different temperature and solvent conditions. Material and Methods: Products were characterized by comparison of physical data with authentic samples and spectroscopic data (IR and NMR). Rate constants are presented as an average of several kinetic runs (at least 6-10) and are reproducible within ± 3%. The overall rate of reaction is followed by monitoring the absorbance changes of the products versus time on a Varian (Model Cary Bio- 300) UV-vis spectrophotometer with a 10 mm light-path cell. Results: The best result was achieved in the presence of 0.075 g (0.1 M) of catalyst and 5 mL methanol at ambient temperature. When the reaction was carried out under solvent-free conditions, the product was obtained in a moderate yield (25%). Methanol was optimized as a desirable solvent in the synthesis of piperidine, nevertheless, ethanol in a kinetic investigation had none effect on the enhancement of the reaction rate than methanol. Based on the spectral data, the overall order of the reaction followed the second order kinetics. The results showed that the first step of the reaction mechanism is a rate determining step. Conclusion: The use of tartaric acid has many advantages such as mild reaction conditions, simple and readily available precursors and inexpensive catalyst. The proposed mechanism was confirmed by experimental results and a steady state approximation.

scholarly journals Clean one-pot multicomponent synthesis of pyrans using a green and magnetically recyclable heterogeneous nanocatalyst

SynOpen ◽  
2021 ◽  
Author(s):  
Mina Ghassemi ◽  
Ali Maleki
Keyword(s):  
Room Temperature ◽  
Significant Loss ◽  
Copper Ferrite ◽  
Multicomponent Synthesis ◽  
Thermo Gravimetric ◽  
Sem Images ◽  
One Pot ◽  
Three Component Reaction ◽  
Ft Ir ◽  
The One

Copper ferrite (CuFe2O4) magnetic nanoparticles (MNPs) were synthesized via thermal decomposition method and applied as a reusable and green catalyst in the synthesis of functionalized 4H-pyran derivatives using malononitrile, an aromatic aldehyde and a β-ketoester in ethanol at room temperature. Then it was characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX) analysis, scanning electron microscopy (SEM) images, thermo gravimetric and differential thermo gravimetric (TGA/DTG) analysis. The catalyst was recovered from the reaction mixture by applying an external magnet and decanting the mixture. Recycled catalyst was reused for several times without significant loss in its activity. Running the one-pot three-component reaction at room temperature, no use of eternal energy source and using a green solvent provide benign, mild, and environmentally friendly reaction conditions; as well, ease of catalyst recovering, catalyst recyclability, no use of column chromatography and good to excellent yields are extra advantages of this work.

scholarly journals A new one-pot three-component synthesis of 4-aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation

Synthesis ◽  
2021 ◽  
Author(s):  
Muhammad Syafiq Bin Shahari ◽  
Ahmad Junaid ◽  
Edward R. T. Tiekink ◽  
Anton V. Dolzhenko
Keyword(s):  
Microwave Irradiation ◽  
Aromatic Aldehydes ◽  
Antileukemic Activity ◽  
One Pot ◽  
Biological Screening ◽  
X Ray ◽  
X Ray Crystallography ◽  
Cyclic Amines ◽  
Three Component Reaction ◽  
Fast Synthesis

A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) to the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-(3,4-dihydroisoquinolin-2(1<i>H</i>)-yl)-4-phenyl-1,3,5-triazin-2-amine.

Application of Fe3O4@SiO2/(CH2)3-[imidazolium-SO3H]Cl as a robust, magnetically recoverable solid acid catalyst for the facile preparation of arylbispyranylmethanes

2017 ◽  
Vol 95 (12) ◽  
pp. 1248-1252 ◽  
Author(s):  
Mohammad Ali Zolfigol ◽  
Mahdiyeh Navazeni ◽  
Meysam Yarie ◽  
Roya Ayazi-Nasrabadi
Keyword(s):  
Effective Potential ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Aromatic Aldehydes ◽  
Core Shell ◽  
Synthetic Procedure ◽  
Three Component Reaction ◽  
Facile Preparation ◽  
Green Conditions

In this study, Fe3O4@SiO2/(CH2)3-[imidazolium-SO3H]Cl shows robust promoting capability in the synthesis of arylbispyranylmethane derivatives under mild and green conditions. Arylbispyranylmethanes were synthesized via efficient three-component reaction of various aromatic aldehydes with 4-hydroxy-6-methyl-2H-pyran-2-one. The nanomagnetic core-shell catalyst presented effective potential of at least eight times recycling applicability in the described synthetic procedure.

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