One-Pot Catalyst-Free Domino Condensation/Intramolecular 1,3-Dipolar Cycloaddition: Highly Stereoselective Access to Phosphadihydrocoumarin-Fused N,N-Bicyclic Pyrazolidin-3-ones

Synthesis ◽  
2017 ◽  
Vol 50 (01) ◽  
pp. 139-145 ◽  
Author(s):  
Mingshu Wu ◽  
Jie Jiang ◽  
Zhongxiang Zhu ◽  
Qinghe Wang ◽  
Dulin Kong
Keyword(s):  
Low Cost ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Nitrogen And Phosphorus ◽  
One Pot ◽  
Intramolecular Cycloaddition ◽  
Catalyst Free ◽  
Synthetic Strategy ◽  
The One ◽  
High Stereoselectivity

A concise, atom-economic, and highly regio/stereoselective synthetic strategy was developed for the construction of phosphorus- and nitrogen-fused polycyclic skeleton derivatives. The one-pot, two-step, catalyst-free domino condensation/intramolecular cycloaddition reaction of various substituted 2-(vinylphosphoryloxy)benzaldehydes with pyrazolidin-3-one took place at room temperature. Three new bonds (C–C, 2 × C–N) and two new nitrogen and phosphorus heterocycles were simultaneously constructed. The reaction is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.

CuI-Catalyzed [3+2] Cycloaddition of Hindered Vinylidenebisphosphonates (VBP) with Azomethine Imines for Highly Regioselective Access to Dinitrogen-Heterobicycle-Containing Bisphosphonates

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2601-2607
Author(s):  
Zhongxiang Zhu ◽  
Qinghe Wang ◽  
Dulin Kong ◽  
Tiao Huang ◽  
Mingshu Wu
Keyword(s):  
Biological Activity ◽  
Low Cost ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Atom Economy ◽  
Mild Conditions ◽  
Synthetic Strategy ◽  
Fused Heterocycles ◽  
Azomethine Imines ◽  
High Stereoselectivity

A concise, atom-economic, and highly regioselective synthetic strategy for the construction of several dinitrogen-fused heterocycles bearing bisphosphonates by 1,3-dipolar cycloaddition reaction of azomethine imines with tetraethyl vinylidene-1,1-bisphosphonate in the presence of CuI in toluene media has been developed. The targeted compounds were obtained in good yields and with excellent regioselectivity. This method for the synthesis of gem-bisphosphonates (BPs) is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.

Direct access to stabilized CuI using cuttlebone as a natural-reducing support for efficient CuAAC click reactions in water

RSC Advances ◽  
2016 ◽  
Vol 6 (68) ◽  
pp. 63613-63623 ◽  
Author(s):  
Sara S. E. Ghodsinia ◽  
Batool Akhlaghinia ◽  
Roya Jahanshahi
Keyword(s):  
Heterogeneous Catalyst ◽  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Click Reactions ◽  
Highly Active ◽  
The One ◽  
Reaction In Water

Cuttlebone@CuCl2 as a highly active, versatile, and green heterogeneous catalyst was investigated for the efficient preparation of 1,4-disubstituted 1,2,3-triazoles through the one-pot Huisgen 1,3-dipolar cycloaddition reaction in water.

scholarly journals Novel Synthesis of Vegetable Oil Derived Corrosion Inhibitors

2015 ◽  
Vol 2015 ◽  
pp. 1-7
Author(s):  
Paul Rostron ◽  
Sonia Kasshanna
Keyword(s):  
Corrosion Inhibitors ◽  
Linseed Oil ◽  
Low Cost ◽  
Reduction Factor ◽  
One Pot ◽  
Chemically Modified ◽  
Synthetic Strategy ◽  
Naturally Occurring ◽  
Cress Seed ◽  
The One

Two different naturally occurring vegetable oils, Cress seed oil, and Linseed oil were chemically modified via novel one pot synthesis to produce fatty acid derived amides. These were characterized by their ability to prevent corrosion of carbon steel in vigorously stirred, aerated seawater, one of the most corrosive naturally occurring environments. Corrosion inhibitor efficiencies of up to 99.6% or a corrosion rate reduction factor of 250 in this medium is reported. The one pot synthetic strategy means that the corrosion inhibitors can be made at very low cost.

1-(2′-Benzimidazolylmethyl)-pyridinium ylide in the one-pot synthesis of indolizine and benzimidazo[1,2-a]pyridine derivatives

2015 ◽  
Vol 70 (8) ◽  
pp. 555-561 ◽  
Author(s):  
Roumaissa Belguedj ◽  
Sofiane Bouacida ◽  
Hocine Merazig ◽  
Ali Belfaitah ◽  
Abdelmalek Bouraiou
Keyword(s):  
Nmr Spectroscopy ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridine Derivatives ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Dimethyl Maleate ◽  
The One ◽  
Pyridinium Ylide

AbstractFour indolizine derivatives were obtained via 1,3-dipolar cycloaddition reaction of 1-(2′-benzimidazolylmethyl)pyridinium ylide with various electron-deficient alkynes. The reaction of this pyridinium N-ylide with dimethyl maleate gave an unexpected methyl 1-oxo-benzimidazo[1,2-a]pyridine-3-carboxylate. The structures of all reported compounds have been examined by X-ray crystallography and NMR spectroscopy.

Copper-catalyzed Convenient Synthesis and SAR Studies of Substituted-1,2,3-triazole as Antimicrobial Agents

2018 ◽  
Vol 16 (1) ◽  
pp. 3-10
Author(s):  
Aniket P. Sarkate ◽  
Kshipra S. Karnik ◽  
Pravin S. Wakte ◽  
Ajinkya P. Sarkate ◽  
Ashwini V. Izankar ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Triazole Derivatives ◽  
Sar Studies ◽  
Convenient Synthesis ◽  
Antibacterial And Antifungal

Background:A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent.Objective:We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity.Methods:A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively.Results and Conclusion:From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.

scholarly journals General synthetic strategy for regioselective ultrafast formation of disulfide bonds in peptides and proteins

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Shay Laps ◽  
Fatima Atamleh ◽  
Guy Kamnesky ◽  
Hao Sun ◽  
Ashraf Brik
Keyword(s):  
Drug Discovery ◽  
Disulfide Bonds ◽  
Unsolved Problem ◽  
De Novo ◽  
Therapeutic Potential ◽  
Selective Activation ◽  
One Pot ◽  
Synthetic Strategy ◽  
The One ◽  
Game Changer

AbstractDespite six decades of efforts to synthesize peptides and proteins bearing multiple disulfide bonds, this synthetic challenge remains an unsolved problem in most targets (e.g., knotted mini proteins). Here we show a de novo general synthetic strategy for the ultrafast, high-yielding formation of two and three disulfide bonds in peptides and proteins. We develop an approach based on the combination of a small molecule, ultraviolet-light, and palladium for chemo- and regio-selective activation of cysteine, which enables the one-pot formation of multiple disulfide bonds in various peptides and proteins. We prepare bioactive targets of high therapeutic potential, including conotoxin, RANTES, EETI-II, and plectasin peptides and the linaclotide drug. We anticipate that this strategy will be a game-changer in preparing millions of inaccessible targets for drug discovery.

Rapid Access to Novel 1,2,3-Triazolo-Heterocyclic Scaffolds via Tandem Knoevenagel Condensation/Azide–Alkyne 1,3-Dipolar Cycloaddition Reaction in One Pot

2014 ◽  
Vol 16 (9) ◽  
pp. 466-477 ◽  
Author(s):  
Ram Awatar Maurya ◽  
Praveen Reddy Adiyala ◽  
D. Chandrasekhar ◽  
Chada Narsimha Reddy ◽  
Jeevak Sopanrao Kapure ◽  
...  
Keyword(s):  
Knoevenagel Condensation ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Rapid Access

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

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