Molecular diversity of the three-component reaction of α-amino acids, dialkyl acetylenedicarboxylates and N-substituted maleimides

2016 ◽  
Vol 14 (27) ◽  
pp. 6497-6507 ◽  
Author(s):  
Liang Chen ◽  
Jing Sun ◽  
Ju Xie ◽  
Chao-Guo Yan
Keyword(s):  
Amino Acids ◽  
Molecular Diversity ◽  
One Pot ◽  
Dialkyl Acetylenedicarboxylate ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction ◽  
The One

The one-pot three-component reaction of secondary α-amino acids with dialkyl acetylenedicarboxylate and N-substituted maleimides afforded functionalized pyrrolo[3,4-a]pyrrolizines, pyrrolo[3′,4′:3,4]pyrrolo[1,2-c]thiazoles, pyrrolo[3,4-a]indolizines and octahydropyrrolo[3,4-c]pyrroles.

scholarly journals Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5493
Author(s):  
Reagan L. Mohlala ◽  
Elena Mabel Coyanis ◽  
Muhammad Q. Fish ◽  
Manuel A. Fernandes ◽  
Moira L. Bode
Keyword(s):  
Membered Ring ◽  
One Pot ◽  
Dialkyl Acetylenedicarboxylate ◽  
Reaction Method ◽  
Dialkyl Acetylenedicarboxylates ◽  
Acidic Proton ◽  
Three Component Reaction ◽  
Two Component

A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported. Reaction of an isocyanide and dialkyl acetylenedicarboxylate with 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and an internal nucleophile gave the products in good yields of 76–85%. The reactivity of dialkyl acetylenedicarboxylates was further tested in the synthesis of thiazole-pyrimidines where a two-component reaction of 2-aminothiazole with dialkyl acetylenedicarboxylates was successfully converted to a more efficient three-component reaction of a thiourea, α-haloketone and dialkyl acetylenedicarboxylate (DMAD/DEtAD) to give thiazole-pyrimidines in good yields of 70–91%.

Intramolecular Diels–Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles

Synthesis ◽  
2019 ◽  
Vol 51 (15) ◽  
pp. 2936-2944 ◽  
Author(s):  
Abdolali Alizadeh ◽  
Kaveh Amir Ashjaee Asalemi ◽  
Mohammadreza Halvagar
Keyword(s):  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Second Step ◽  
Cycloaddition Reactions ◽  
One Pot ◽  
Dialkyl Acetylenedicarboxylate ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
Final Compound ◽  
The One

A one-pot approach for the synthesis of epoxypyrrolo[3,4-g]indazoles is presented. The first step was initiated by a three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and 2-furancarboxylic acid, and led to 1,3-dioxoepoxyisoindole, followed by the addition of hydrazonoyl chloride through a [3+2]-cycloaddition reaction in the second step. The key step in the formation of final compound involves a bicyclization strategy through intramolecular Diels–Alder­ (IMDA) reaction.

Synthesis of Unsymmetrical 1,4-dihydropyridines from Dialkyl Acetylenedicarboxylates, Amines and Arylidenemalononitriles Promoted by Potassium Carbonate

2016 ◽  
Vol 40 (12) ◽  
pp. 750-752 ◽  
Author(s):  
Hossein Mehrabi ◽  
Hadi Tavakolian
Keyword(s):  
Potassium Carbonate ◽  
Chromatographic Separation ◽  
One Pot ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction ◽  
The One

The one-pot, three-component reaction of dialkyl acetylenedicarboxylates, arylamines and arylidenemalononitriles in the presence of potassium carbonate in acetonitrile at 50 °C afforded 11 6-amino-5-cyano-1,4-dihydropyridine-2,3-dicarboxylates, nine of which are novel. These conditions offer simplified operation, easy purification and good yields. Also, this method avoids the use of expensive catalysts, toxic solvents and chromatographic separation.

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 Water-Soluble Copper-Immobilized Covalent Organic Framework Functioning as an “OFF–ON” Fluorescent Sensor for Amino Acids

2021 ◽  
Author(s):  
Lamiaa Reda Ahmed ◽  
Ahmed F. M. EL-Mahdy ◽  
Cheng-Tang Pan ◽  
Shiao-Wei Kuo
Keyword(s):  
Amino Acids ◽  
Fluorescent Sensor ◽  
Water Soluble ◽  
One Pot ◽  
Covalent Organic Framework ◽  
The One ◽  
Organic Framework

In this paper, we describe the construction of a new fluorescent hydroxyl- and hydrazone-based covalent organic framework (TFPB-DHTH COF) through the one-pot polycondensation of 1,3,5-tris(4-formylphenyl)benzene (TFPB) and 2,5-dihydroxyterephthalohydrazide (DHTH) under...

Silica sulfuric acid magnetic nanoparticle: an efficient and ecofriendly catalyst for synthesis of spiro[2-amino-4H-pyran-oxindole]s

2015 ◽  
Vol 93 (5) ◽  
pp. 546-549 ◽  
Author(s):  
Ali Reza Karimi ◽  
Meysam Sourinia ◽  
Zeinab Dalirnasab ◽  
Marzie Karimi
Keyword(s):  
Sulfuric Acid ◽  
Magnetic Nanoparticle ◽  
Ultrasound Irradiation ◽  
Significant Loss ◽  
Silica Sulfuric Acid ◽  
One Pot ◽  
External Magnet ◽  
Three Component Reaction ◽  
The One ◽  
High Yields

Silica sulfuric acid magnetic nanoparticles efficiently catalyze the one-pot, three-component reaction of isatins and malononitrile with dimedone, 1,3-dimethylbarbituric acid or 4-hydroxycoumarin in EtOH–H2O to afford the corresponding spiro[2-amino-4H-pyran-oxindole] derivatives in high yields under ultrasound irradiation at 60 °C. The heterogeneous nanocatalyst could be recovered easily from the reaction mixture using an external magnet and reused many times without significant loss of its catalytic activity.

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.

One-pot synthesis of 3-aminofurans using a simple and efficient recyclable CuI/[bmim]PF6 system

2021 ◽  
Author(s):  
Guguloth Veeranna ◽  
Ramesh Balaboina ◽  
Narasimha Swamy Thirukovela ◽  
Ravindhar Vadde
Keyword(s):  
Secondary Amines ◽  
Terminal Alkynes ◽  
One Pot ◽  
One Pot Synthesis ◽  
System P ◽  
Three Component Reaction ◽  
The One

The one-pot three-component reaction of several 2-ketoaldehdyes, secondary amines and terminal alkynes to access 3-aminofurans was proceeded well in [bmim][PF6] using a simple and cheap CuI catalyst. The resulted 3-aminofuran...

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