Nucleophilic Phosphine-Promoted Domino Reaction of Dialkyl Acetylenedicarboxylates and 3-Arylamino-1-methyl-1H-pyrrole-2,5-diones

Synthesis ◽  
2018 ◽  
Vol 50 (18) ◽  
pp. 3715-3722 ◽  
Author(s):  
Ying Han ◽  
Chao-Guo Yan ◽  
Chang-Zhou Liu ◽  
Yuan-Yuan Zhang ◽  
Jing Sun
Keyword(s):  
Room Temperature ◽  
Domino Reaction ◽  
Dimethyl Acetylenedicarboxylate ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction

The three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 at room temperature resulted in functionalized 3-(triphenyl-λ5-phosphanylidene)succinates in nearly quantitative yields. However, tri(n-butyl)phosphine promoted reaction of dialkyl acetylenedicarboxylates and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 afforded functionalized pyrrolo[3,4-b]pyridine-4-carboxylates in satisfactory yields.

scholarly journals A Facile Synthesis of Polysubstituted Pyrroles by One-Pot Three-Component Reaction

2012 ◽  
Vol 9 (4) ◽  
pp. 2239-2244 ◽  
Author(s):  
Hossein Anaraki-Ardakani ◽  
Maziar Noei ◽  
Mina Karbalaei-Harofteh ◽  
Shahab Zomorodbakhsh
Keyword(s):  
Room Temperature ◽  
Facile Synthesis ◽  
One Pot ◽  
Pyrrole Derivatives ◽  
Dialkyl Acetylenedicarboxylates ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields ◽  
Neutral Conditions

A new and efficient one-pot synthesis of polysubstituted pyrrole derivatives by three-component reaction between dialkyl acetylenedicarboxylates, triphenylphosphine, 2-aminopyridin derivatives in the presence of arylglyoxals is described. The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded high yields of products.

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

scholarly journals An Efficient Isocyanide-Based Three-Component Synthesis of Novel Ketenimines

2014 ◽  
Vol 10 (3) ◽  
pp. 2363-2368
Author(s):  
Hamideh Emtiazi ◽  
Mohammad Ali Amrollahi
Keyword(s):  
Room Temperature ◽  
Simple Procedure ◽  
Reaction Times ◽  
Dimethyl Acetylenedicarboxylate ◽  
One Pot ◽  
Three Component Reaction ◽  
High Yields

This study provides a description of an efficient and simple procedure for the synthesis of dimethyl 2-(9-aryl)-3,3,6,6-tetramethyl-1,8-diox-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)-3-((cyclohexylimino)methylene)succinate via a one-pot three-component reaction of cyclohexyl isocyanide, dimethyl acetylenedicarboxylate and hexahydroacridine-1,8(2H,5H)-dionesin CH2Cl2 at room temperature. Short reaction times, good to high yields and the novelty are the remarkable advantages of this work.

Solvent-free Synthesis of 1,2-Disubstituted Derivatives of 1,2- Dihydroisoquinoline, 1,2-Dihydroquinoline and 1,2-Dihydropyridine

2013 ◽  
Vol 68 (7) ◽  
pp. 818-822 ◽  
Author(s):  
Rahimeh Hajinasiri ◽  
Sobhan Rezayati
Keyword(s):  
Room Temperature ◽  
Solvent Free ◽  
Reaction Conditions ◽  
One Pot ◽  
Efficient Approach ◽  
Dialkyl Acetylenedicarboxylates ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
Derivatives Of ◽  
Solvent Free Synthesis

A one-pot and efficient approach to the synthesis of dialkyl 2-[1-[(alkoxycarbonyl)anilino]-2(1H)- (isoquinolin-2-yl) (or -quinolin-1-yl or -pyridin-1-yl)]-2-butenedioates is described. This method involves a three-component reaction between isoquinoline, quinoline or pyridine, dialkyl acetylenedicarboxylates and N-phenylcarbamates under solvent-free conditions, without using any catalyst and at room temperature. The mild reaction conditions and good yields of the products exhibit the synthetic advantage of this method.

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 The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 581
Author(s):  
Max Van Hoof ◽  
Santhini Pulikkal Veettil ◽  
Wim Dehaen
Keyword(s):  
Room Temperature ◽  
Aromatic Ketones ◽  
Three Component Reaction ◽  
Reaction Proceeds

4-Sulfonyl-1,2,3-triazole scaffolds possess promising bioactivities and applications as anion binders. However, these structures remain relatively unexplored and efficient synthetic procedures for their synthesis remain desirable. A practical room-temperature, aerobic copper-catalyzed three-component reaction of aromatic ketones, sodium sulfinates, and azides is reported. This procedure allows for facile access to 4-sulfonyl-1,5-disubstituted-1,2,3-triazoles in yields ranging from 34 to 89%. The reaction proceeds via a sequential aerobic copper(II)chloride-catalyzed oxidative sulfonylation and the Dimroth azide–enolate cycloaddition.

Visible-light-promoted sulfonylation of thiols with aryldiazonium and sodium metabisulphite leading to unsymmetrical thiosulfonates

2021 ◽  
Author(s):  
Yu-Fen Lv ◽  
Jinyun Luo ◽  
Yuchuan Ma ◽  
Qi Dong ◽  
Lin He
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Metal Free ◽  
Sodium Metabisulphite ◽  
Three Component Reaction

A new visible-light-mediated protocol has been proposed for the synthesis of thiosulfonates via metal-free sulfonylation of thiols with aryldiazonium and sodium metabisulphite at room temperature. This mild three-component reaction, simply...

ChemInform Abstract: Three-Component Reaction Between Alkyl(aryl) Isocyanides and Dialkyl Acetylenedicarboxylates in the Presence of Ethyl Trifluoroacetate.

ChemInform ◽  
2011 ◽  
Vol 42 (40) ◽  
pp. no-no
Author(s):  
Khatereh Khandan-Barani ◽  
Malek Taher Maghsoodlou ◽  
Sayyed Mostafa Habibi-Khorasani ◽  
Nourallah Hazeri ◽  
Seyyed Sajad Sajadikhah
Keyword(s):  
Alkyl Aryl ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction

scholarly journals Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

2013 ◽  
Vol 9 ◽  
pp. 8-14 ◽  
Author(s):  
Yan Sun ◽  
Jing Sun ◽  
Chao-Guo Yan
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Room Temperature ◽  
The Other ◽  
Other Hand ◽  
Three Component Reaction ◽  
High Yields

A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.

Aqueous, One-Pot, Three-Component Reaction for Efficient Synthesis of 2-[4-(Arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, ‑1H-benzimidazole, or -1,3-benzoxazole Derivatives

Synlett ◽  
2017 ◽  
Vol 28 (17) ◽  
pp. 2295-2298
Author(s):  
Kommula Dileep ◽  
M. Murty
Keyword(s):  
Room Temperature ◽  
Efficient Synthesis ◽  
One Pot ◽  
Three Component Reaction ◽  
Aqueous Conditions

A simple and efficient synthetic protocol has been developed involving a one-pot three-component reaction of a 2-chlorobenzazole, piperazine, and an arenesulfonyl chloride under aqueous conditions at room temperature in the absence of a catalyst, ligand, or base. By using this protocol, a variety of 2-[4-(arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, -1H-benzimidazole, and -1,3-benzoxazole derivatives were synthesized in excellent yields.

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