scholarly journals A Convenient Synthesis and Antibacterial Activity of Novel α-Aminophosphonic Acid Esters from Amino Acids/Esters (Kabachnik-Fields Reaction)

2008 ◽  
Vol 5 (4) ◽  
pp. 679-687 ◽  
Author(s):  
CH. Mohan ◽  
B. Hari Babu ◽  
C. Naga Raju ◽  
R. Usha Nagalakshmi
Keyword(s):  
Amino Acids ◽  
Antibacterial Activity ◽  
Aromatic Aldehydes ◽  
Aminophosphonic Acid ◽  
One Pot ◽  
Mass Spectral ◽  
Convenient Synthesis ◽  
Three Component Reaction ◽  
High Yields ◽  
Acid Esters

Synthesis of novel α-aminophosphonic acid esters (5a-n) were achieved with high yields through one-pot three component reaction process by Kabachnik-Fields reaction. It involves the reaction among amino acids/esters, substituted aromatic aldehydes and dialkyl phosphites in absolute ethanol at reflux temperature. Their structures were established by elemental analysis IR,¹H,¹³C,³¹P NMR and mass spectral data. All the title compounds were screened for their antibacterial activity. Most of the compounds exhibited moderate antimicrobial activity.

scholarly journals A Convenient One-pot Synthesis of 2,3-Disubstituted Thieno[2,3-d]pyrimidin-4(3H)-ones from 2H-Thieno[2,3-d][1,3]oxazine-2,4(1H)-diones, Aromatic Aldehydes and Amines

SynOpen ◽  
2018 ◽  
Vol 02 (02) ◽  
pp. 0207-0212 ◽  
Author(s):  
Feize Liu ◽  
Xueling Hou ◽  
Li Nie ◽  
Khurshed Bozorov ◽  
Michael Decker ◽  
...  
Keyword(s):  
Aromatic Aldehydes ◽  
One Pot ◽  
One Pot Synthesis ◽  
Convenient Synthesis ◽  
Three Component Reaction ◽  
Simple Protocol ◽  
High Yields

An efficient, simple protocol has been established for convenient synthesis of novel 2,3-disubstituted thieno[2,3-d]pyrimidin-4(3H)-one derivatives in good to high yields through a one-pot, two-step and three-component reaction from 2H-thieno[2,3-d][1,3]oxazine-2,4(1H)-diones, aromatic aldehydes, and amines.

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.

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.

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.

scholarly journals CeCl3⋅7H2O/SiO2as an Efficient and Recyclable Catalyst for the Synthesis of Dihydropyrano[3,2-b]chromenediones

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Chong Zhang ◽  
Yan Qu
Keyword(s):  
Kojic Acid ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Recyclable Catalyst ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
High Yields

Dihydropyrano[3,2-b]chromenedione derivatives were synthesized in moderate-to-high yields in one-pot three-component reaction from the corresponding aromatic aldehydes, kojic acid, and dimedone, in the presence of catalytic amount ofCeCl3⋅7H2O/SiO2as a nontoxic, reusable, inexpensive, and easily available reagent, under solvent-free conditions.

Synthesis of novel series of 7,7′-(substituted methylene)bis-imidazo[1,2-b]pyrazoles via an acid catalyzed one-pot three-component reaction

2018 ◽  
Vol 42 (8) ◽  
pp. 5728-5741 ◽  
Author(s):  
Mohsine Driowya ◽  
Hassan Allouchi ◽  
José Manuel Gally ◽  
Pascal Bonnet ◽  
Gérald Guillaumet
Keyword(s):  
Aromatic Aldehydes ◽  
Acid Catalysts ◽  
Rapid Synthesis ◽  
One Pot ◽  
Three Component Reaction ◽  
Acid Catalyzed ◽  
High Yields ◽  
Substituted Pyrazoles

An efficient and rapid synthesis of new series of N-alkyl-2-aryl-5H-imidazo[1,2-b]pyrazoles has been achieved in high yields through a three-component reaction of 3-amino-4-substituted pyrazoles, aromatic aldehydes and isocyanides mediated by acid catalysts.

scholarly journals Three-component reaction of β-keto esters, aromatic aldehydes and urea/thiourea promoted by caffeine, a green and natural, biodegradable catalyst for eco-safe Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones derivatives under solvent-free conditions

2018 ◽  
Vol 83 (6) ◽  
pp. 673-684 ◽  
Author(s):  
Farzaneh Mohamadpour ◽  
Mojtaba Lashkari
Keyword(s):  
Biginelli Reaction ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Solid Catalyst ◽  
One Pot ◽  
Keto Esters ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
High Yields

Caffeine was found to be a natural and green and biodegradable catalyst for the one-pot, three-component condensation Biginelli reaction of ?-keto esters, aromatic aldehydes and urea/thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones/thiones derivatives under solvent-free conditions. The remarkable features of this green procedure are high yields, short reaction times, simplicity of operation and work-up procedures, the availability and easy handling of this solid catalyst, avoidance of hazardous or toxic catalysts and organic solvents and economic availability of the catalyst.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

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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