Cyclopropanes in water: a diastereoselective synthesis of substituted 2H-chromen-2-one and quinolin-2(1H)-one linked cyclopropanes

2016 ◽  
Vol 18 (7) ◽  
pp. 2201-2205 ◽  
Author(s):  
Ashish Anand ◽  
Jayashree Yenagi ◽  
J. Tonannavar ◽  
Manohar V. Kulkarni
Keyword(s):  
Aromatic Aldehydes ◽  
Diastereoselective Synthesis ◽  
One Pot ◽  
Three Component Reaction ◽  
Substituted Cyclopropanes

A one-pot three component reaction has been developed for the synthesis of substituted cyclopropanes employing 4-bromomethyl-2H-chromen-2-one/quinolin-2(1H)-ones, aromatic aldehydes and activated nitriles.

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.

scholarly journals Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®)

Chemistry ◽  
2020 ◽  
Vol 2 (2) ◽  
pp. 600-612
Author(s):  
Valentina Varga ◽  
Péter Ábrányi-Balogh ◽  
Mátyás Milen
Keyword(s):  
High Temperature ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Optimal Procedure ◽  
Three Component Reaction

A sequential one-pot two-step protocol has been elaborated for the synthesis of naphthoxazinones from 2-naphthol, methyl carbamate, and aromatic aldehydes. First, a three-component reaction was optimized with the dehydrating additive propylphosphonic anhydride (T3P®), resulting in 1-carbamatoalkyl 2-naphthols in good to excellent yields. Following the successful multicomponent approach, intramolecular acylation was performed at high temperature, again with the contribution of T3P®, resulting in naphthoxazinone derivatives in moderate yields. These two steps were optimized together in one-pot as well, and the sequential rise in the requisite temperature eventuated the optimal procedure for the multistep cascade.

ChemInform Abstract: An Efficient and Diastereoselective Synthesis of Hydrazino Amides via a Novel One-Pot Three-Component Reaction.

ChemInform ◽  
2013 ◽  
Vol 44 (35) ◽  
pp. no-no
Author(s):  
Sorour Ramezanpour ◽  
Saeed Balalaie ◽  
Frank Rominger ◽  
Hamid Reza Bijanzadeh
Keyword(s):  
Diastereoselective Synthesis ◽  
One Pot ◽  
Three Component Reaction

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.

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.

Ultrasonic Activated, Highly Efficient and Regioselective Synthesis of a Novel Pyrrole- Linked benzo[f]chromene Scaffold in a Green Media

2018 ◽  
Vol 15 (6) ◽  
pp. 872-880 ◽  
Author(s):  
Fateme Tavakoli ◽  
Manouchehr Mamaghani ◽  
Mehdi Sheykhan ◽  
Narjes Mohammadipour ◽  
Mehdi Rassa
Keyword(s):  
Antibacterial Activity ◽  
Single Molecule ◽  
Aromatic Aldehydes ◽  
Model Reaction ◽  
Conventional Heating ◽  
Initial Attempt ◽  
One Pot ◽  
Green Protocol ◽  
Three Component Reaction ◽  
The Impact

Aim and Objective: Chromene scaffold is one of the most famous oxygen heterocycles that have widely found in plants playing pivotal roles in medicinal and synthetic chemistry. This study was undertaken to provide a green protocol for the synthesis of novel functionalized chromen-pyrrole hybrids by a regioselective three-component reaction via both conventional and sonochemical methods. Because of fascinating features of these individual cores, a hybride molecular structure comprising of pyrrole and chromene moieties could result in a novel single molecule with increased efficacy. Materials and Methods: The synthesis of novel functionalized chromen-pyrrole hybrids was accomplished by regioselective three-component reaction of β-naphthol, 3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile and diverse aromatic aldehydes catalyzed by triethylamine in H2O-EtOH via both conventional and sonochemical methods. The impact of some variants such as solvents, catalysts and temperature was also probed under both conventional heating and sonochemical methods to accomplish the optimized reaction condition. The synthesized products were screened for antibacterial activity against Gram positive (Ml, Bs, Sa) and Gram negative bacteria (Ps, Ec). Results: In initial attempt, the reaction of equimolar amounts of 2-fluorobenzaldehyde, 3-(1-methyl-1H-pyrrol- 2-yl)-3-oxopropanenitrile and β-naphthol was selected as a model reaction. The role of various solvents, temperature and different acidic and basic catalysts on the model reaction was examined. The optimized condition was the use of 20 mol% triethylamine in H2O-EtOH (1:1) under ultrasound irradiation at 65°C. The scope of this reaction was screened with respect to various substituted aromatic aldehydes. Considering the results, the electronic features of substituents affected the performance of this condensation. The reaction with aromatic aldehydes containing electron-withdrawing groups proceeded in lower reaction time, affording the productds in high to excellent yields while aldehydes with electron-donating groups reacted more slowly. This three-component reaction also provided a suitable procedure for the synthesis of bis-(chromen-pyrrole) in excellent yield. All of the synthesized products had significant antibacterial activity against the screened bacteria (Ml, Bs, Sa, Ps, Ec). Conclusion: A streamlined, regioselective and ecofriendly ultrasonic-promoted procedure for the synthesis of novel substituted benzo[f]chromenes from one-pot condensation of β-naphthol, 3-(1-methyl-1H-pyrrol-2-yl)-3- oxopropanenitrile and structurally diverse aldehydes catalyzed by triethylamine was developed. This green protocol furnishes all the products in reduced reaction times and high yields. In addition, the synthesized novel compounds showed narrow to wide spectral activity against the tested strains.

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 Ceric Ion Loaded MCM-41 Catalyzed Synthesis of Substituted Mono- and Bis-dihydropyrimidin-2(1H)-ones

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
Pullar Vadivel ◽  
Rathinam Ramesh ◽  
Appaswami Lalitha
Keyword(s):  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Solvent Free Condition ◽  
Three Component Reaction ◽  
High Yields ◽  
Work Up ◽  
Mcm 41

An effective one-pot three-component reaction of aromatic aldehydes with 1,3-diketone and urea or thiourea under solvent-free condition leads to the formation of mono- and bis-dihydropyrimidin-2-(1H)-ones using Ce-MCM-41 as a recyclable solid acid catalyst. This method has several advantages like simple and easy work-up with shorter reaction time, reusability of catalyst, and high yields of Biginelli products.

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.

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 267-271 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Atiyeh Moafi ◽  
Behzad Jafari ◽  
Alexander Vilinger ◽  
Peter Langer
Keyword(s):  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
Relative Stereochemistry ◽  
High Yields

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

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