Microwave-assisted Three-component Reaction Research Articles

Magnetically recoverable nanocatalyst for the synthesis of pyranopyrazoles: CoFe2O4@SiO2-HClO4

The multiheterocyclic ring system shows valuable pharmaceutical and biological activities. In the present study, a microwave-assisted three-component reaction between aryl aldehyde, malononitrile, and 5-methyl-2,4-dihydro-3H-pyrazole-3-one led to the synthesis of pyrano[2,3-c]pyrazoles has been described. The reaction was carried out under solvent-free conditions in the presence of a new magnetically recoverable nanocatalyst (CoFe2O4@SiO2-HClO4). The reported protocol offers several advantages such as being environmentally benign, being rapid, inexpensive, having high atom and step economy, and being facile. The simple method of catalyst preparation, easy magnetic recovery, and reusability of the catalyst for four runs are notable features of the nanocatalyst. Antibacterial activity of all synthesized compounds was tested against Escherichia coli and Staphylococcus aureus. All synthesized compounds showed promising biological activity and may be used as a potential antibacterial candidate in biological science.

Synthesis and Cytotoxic Evaluation of Fluoro and Trifluoromethyl Substituents Containing Novel Naphthoquinone-Fused Podophyllotoxins

A series of novel naphthoquinone-fused podophyllotoxins containing fluoro and trifluoromethyl substituents were synthesized in a medium with good yields using two different synthetic approaches: microwave-assisted four-component reactions of 2-hydroxy-1,4-naphthoquinone, tetronic acid, fluorinated arylaldehydes, and ammonium acetate, and microwave-assisted three-component reactions of 2-amino-1,4-naphthoquinone, tetronic acid, and fluorinated arylaldehydes. The structures of all products were confirmed by spectral analysis. Together, cytotoxicity assessment of the products against four human cancer cell lines (human carcinoma [KB], human hepatocellular carcinoma [HepG2], lung cancer [A549], breast carcinoma [MCF7], and human embryonic kidney [Hek-293]) was performed by MTT assay. Among the obtained compounds, compound 7f turned out to be the most potent anticancer agent with significant cytotoxic activity against KB, HepG2, and MCF cancer cell lines.

Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds.

A new approach for the synthesis of podophyllotoxin-naphthoquinone compounds using microwave-assisted three-component reactions is reported in this study. Novel podophyllotoxin-naphthoquinone derivatives with modification on ring E were synthesized. All the synthetic compounds were assessed in terms of their cytotoxicity profile against four cancer cell lines (KB, HepG2, A549, and MCF7), and noncancerous Hek-293 cell lines. Notably, treatment of SK-LU-1 cells with compounds 5a and 5b resulted in G2/M phase arrest of the cell cycle, caspase-3/7 activation, and apoptosis. Additionally, molecular docking studies were performed and showed important interaction of two compounds against residues in the colchicine-binding-site of tubulin as well. Taken together, compounds 5a and 5b were identified as potent anticancer agents.

4-(Dimethylamino)pyridine as an Efficient Catalyst for One-Pot Synthesis of 1,4-Pyranonaphthoquinone Derivatives viaMicrowave-Assisted Sequential Three Component Reaction in Green Solvent

Novel 1,4-pyranonaphthoquinone derivatives were successfully synthesized via the microwave-assisted three-component reaction of 1,4-naphthoquinone, malononitrile, and various arylaldehydes in ethanol in the presence of 4-(dimethylamino)pyridine (DMAP) as a catalyst, and subsequently evaluated in terms of their antimicrobial and antifungal activities. This synthetic procedure has the notable advantages of environmental friendliness, short reaction time, good yield, and convenient operation.

Synthesis of novel 3-arylated 2-hydroxy-1,4-naphthoquinone derivatives via microwave-assisted three-component domino reaction and evaluation of their cytotoxic activity

Synthesis of novel 3-arylated 2-hydroxy-1,4-naphthoquinone derivatives via microwave-assisted three-component reaction starting from 2-hydroxy-1,4-naphthoquinone, tetronic acid, and various aromatic aldehydes has been described. This multicomponent domino reaction proceeded through the Knoevenagel condensation, Michael addition, deprotonation, and 1,3-H shift steps. Five of the synthesized compounds displayed good cytotoxic activity against two human cancer cell lines, KB and HepG2, with half maximal inhibitory concentration values in a range of 4–20 μM.

Synthesis of penta- and tetra-cyclic cage-like compounds and dispiro heterocycles through microwave-assisted solvent-free multi-component domino reactions

Novel penta- and tetra-cyclic cage-like compounds and dispiro heterocycles were obtained as a result of a microwave-assisted three-component domino reaction.

Microwave-assisted SiO2-H2SO4-catalyzed Synthesis of 3,4,6,7-Tetrahydro-3,3,6,6-Tetramethyl-9,10-diphenylacridine-1,8-dione Derivatives as Cholesterol Esterase Inhibitors

A library of 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9,10-diphenylacridine-1,8-dione derivatives were synthesized via microwave-assisted three-component reaction employing silica supported sulphuric acid under solvent free conditions and tested for in vitro cholesterol esterase inhibitory activity. All synthesized compounds exhibited moderate to good inhibition of cholesterol esterase enzyme. Among all the synthesized acridinedione derivatives, compound HSM-1a showed the most promising activity with IC50 value of 1.53 µM against cholesterol esterase enzyme. Enzyme kinetic studies carried out for HSM-1a, revealed its mixed-type inhibition approach. Molecular protein–ligand docking studies were also performed to figure out the key binding interactions of HSM-1a with the amino acid residues of the enzyme’s active site. Furthermore, acquiescence of some potent compounds to the Lipinski rule was also determined.

A Sustainable Approach to the Stereoselective Synthesis of Diazaheptacyclic Cage Systems Based on a Multicomponent Strategy in an Ionic Liquid.

The microwave-assisted three-component reactions of 3,5-bis(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones, acenaphthenequinone and cyclic α-amino acids in an ionic liquid, 1-butyl-3-methylimidazolium bromide, occurred through a domino sequence affording structurally intriguing diazaheptacyclic cage-like compounds in excellent yields.

ChemInform Abstract: Microwave‐Assisted Three‐Component Reactions Leading to Pyrano‐Fused Pyrazolo[3,4‐b]pyridines.

A series of pyrano-fused pyrazolo[3,4-b]pyridine derivatives with an aryl group presenting the 2-position of the pyridine nucleus have been synthesized by microwave-assisted three-component reactions of aldehydes, tetrahydropyran-4-one, and 3-methyl-1-phenyl-1H-pyrazol-5-amine in HOAc. This method is very efficient because of short reaction times and easy work-up, and it provides an efficient and promising synthetic strategy for the construction of the tricyclic pyrano-fused pyrazolo[3,4-b]pyridine skeleton.

Microwave-assisted solvent-free synthesis of imidazo[1,2-a]pyridines via a three-component reaction

A facile microwave-assisted three-component reaction of pyridin-2-amine, 3-phenylpropiolaldehyde and alcohol is catalyzed by TsOH under solvent-free conditions to give corresponding imidazo[1,2-a]pyridines in good yields. Reactions proceed with high efficiency and good functional group tolerance. This approach provides a useful protocol for the preparation of functionalized imidazo[1,2-a]pyridine derivatives.

N-methylimidazole mediated synthesis of aryl alkyl ethers under microwave irradiation and solvent free conditions

Microwave-assisted three-component reaction has been established for the synthesis of aryl alkyl ethers. The reaction was carried out under solvent free conditions in the presence of N-methylimidazole and dialkylacetylenedicarboxylate to furnish a novel approach to O-alkylation of phenol derivatives in high yield

Microwave-assisted C–N and C–S bond-forming reactions: an efficient three-component domino sequence for the synthesis of sulfoether-decorated imidazo[1,2-a]pyridines

Microwave-assisted three-component domino reaction for the synthesis of sulfoether-decorated imidazo[1,2-a]pyridines.

Facile and diverse microwave-assisted synthesis of secondary propargylamines in water using CuCl/CuCl2

A highly efficient microwave-assisted three-component reaction between an aldehyde, a primary amine and an alkyne was developed using an inexpensive Cu(i)/Cu(ii) catalytic system and water as solvent.

ChemInform Abstract: A Novel One‐Pot Three‐Component Reaction for the Synthesis of 5‐Arylamino‐pyrrolo[2,3‐d]pyrimidines under Microwave Irradiation.

Some novel 5-arylamino-pyrrolo[2,3-d]pyrimidine derivatives were synthesized via microwave-assisted three-component reaction of N,N-dimethyl-6-aminouracil, aryl glyoxal monohydrates and aryl amines. The products were obtained in good to excellent yields (82–91%) using a simple work-up procedure.

Microwave‐Assisted Aqueous Reactions: An Efficient Route to Benzodiazepines

Microwave-assisted three-component reaction has been established for the synthesis of benzodiazepines. This reaction promoted by HOAc was conducted by using readily available and inexpensive starting materials in water under microwave irradiation. The present green synthesis shows fascinating characteristics such as the use of water as the reaction solution, concise one-pot conditions, short reaction periods, easy purification, and reduced waste production without the use of any strong acids or metal promoters.

A novel one-pot three-component reaction for the synthesis of 5-arylamino-pyrrolo[2,3-d]pyrimidines under microwave irradiation

Some novel 5-arylamino-pyrrolo[2,3-d]pyrimidine derivatives were synthesized via microwave-assisted three-component reaction of N,N-dimethyl-6-aminouracil, aryl glyoxal monohydrates and aryl amines. The products were obtained in good to excellent yields (82–91%) using a simple work-up procedure.

ChemInform Abstract: Facile Access to γ‐Aminothiols from 1,3‐Thiazines via a Microwave‐Assisted Three‐Component Reaction.

ChemInformVolume 44, Issue 10 Preparative Organic Chemistry ChemInform Abstract: Facile Access to γ-Aminothiols from 1,3-Thiazines via a Microwave-Assisted Three-Component Reaction. Flavie Peudru, Flavie Peudru Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this authorRemi Legay, Remi Legay Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this authorJean-Francois Lohier, Jean-Francois Lohier Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this authorVincent Reboul, Vincent Reboul Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this authorMihaela Gulea, Mihaela Gulea Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this author Flavie Peudru, Flavie Peudru Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this authorRemi Legay, Remi Legay Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this authorJean-Francois Lohier, Jean-Francois Lohier Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this authorVincent Reboul, Vincent Reboul Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this authorMihaela Gulea, Mihaela Gulea Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.Search for more papers by this author First published: 07 March 2013 https://doi.org/10.1002/chin.201310028Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume44, Issue10March 5, 2013 RelatedInformation

Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles.

A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.

Facile access to γ-aminothiols from 1,3-thiazines via a microwave-assisted three-component reaction

A new efficient and general synthetic methodology to access γ-aminothiols was investigated and developed. 1,3-Thiazines were used as convenient precursors and were prepared by a fast microwave-assisted three-component reaction (3CR) of thioamides, aldehydes, and alkenes. The transformation of thiazines into aminothiols was achieved via a thiazinium salt hydrolysis, in three very facile steps.

Synthesis of 5-alkylated barbituric acids and 3-alkylated indoles via microwave-assisted three-component reactions in solvent-free conditions using Hantzsch 1,4-dihydropyridines as reducing agents

Reaction of barbituric acids with aldehydes and dihydropyridines in one pot under microwave (MW) irradiation in the absence of solvent, affords 55–82% of the 5-benzylated barbituric acids. Use of alkyl nitriles or barbituric acids with indole-3-aldehyde and dihydropyridine (DHP) afforded 3-alkylated indoles in 57–76 % yield. In each case DHPs are converted to pyridines.