scholarly journals One-Pot, Three-Component Synthesis of 1-(2-Hydroxyethyl)-1H-1,2,3-triazole Derivatives by Copper-Catalyzed 1,3-Dipolar Cycloaddition of 2-Azido Alcohols and Terminal Alkynes under Mild Conditions in Water

2010 ◽  
Vol 93 (3) ◽  
pp. 435-449 ◽  
Author(s):  
Hashem Sharghi ◽  
Mona Hosseini-Sarvari ◽  
Fatemeh Moeini ◽  
Reza Khalifeh ◽  
Alireza Salimi Beni
Keyword(s):  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Triazole Derivatives ◽  
Mild Conditions

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 Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

One-pot synthesis of novel N,N-bis(isoxazol-5-yl)methyl tertiary arylamines via sequential diprop-3-ynylation and 1,3-dipolar cycloaddition from primary amines

2019 ◽  
Vol 43 (9-10) ◽  
pp. 407-411 ◽  
Author(s):  
Xiao-Lan Zhang ◽  
Mei-Hong Wei ◽  
Shou-Ri Sheng ◽  
Xiao-Ling Liu
Keyword(s):  
Primary Amines ◽  
Dipolar Cycloaddition ◽  
Calcium Hydride ◽  
Methyl Groups ◽  
Propargyl Bromide ◽  
One Pot ◽  
Mild Conditions ◽  
Good Product ◽  
Easy Operation

A simple and efficient one-pot multicomponent approach for the synthesis of tertiary arylamines bearing N,N-bis(isoxazol-5-yl)methyl groups is developed through reactions including sequential diprop-3-ynylation of primary amines with propargyl bromide in the presence of calcium hydride in N,N-dimethylformamide, and 1,3-dipolar cycloaddition with nitrile oxides generated in situ from hydroximyl chlorides in DMF-Et3N. This protocol provides advantages such as high regioselectivity, easy operation, and moderate-to-good product yields with a wide substrate scope under mild conditions.

4-(N,N-Dimethylamino)pyridine (DMAP)-Catalyzed 1,3-Dipolar Cycloaddition of 3-Aminooxindole-Based Azomethine Ylides with α,β-Unsaturated Acyl Phosphonates for the Construction of Spiropyrrolidinyl-2,3′-oxindoles

Synthesis ◽  
2018 ◽  
Vol 51 (06) ◽  
pp. 1353-1364 ◽  
Author(s):  
Zhuo Chen ◽  
Lin Chen ◽  
Jin He ◽  
Rong-Guo Sun ◽  
Li Fan ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Mild Conditions ◽  
Unsaturated Acyl ◽  
Brønsted Base

A novel, one-pot 1,3-dipolar cycloaddition of 3-amimooxindole-based azomethine ylides with α,β-unsaturated acyl phosphonates and subsequent derivatization of the intermediates is described. Employing 4-(N,N-dimethylamino)pyridine (DMAP), an organic Brønsted base, as a robust catalyst leads to an architecturally diverse set of spiropyrrolidinyl-2,3′-oxindoles bearing four contiguous stereocenters and an ester or an amide at the γ-position of the pyrrolidine motif. The products are obtained in moderate to excellent yields and with good diastereoselectivities under mild conditions. The potential of this methodology is demonstrated through a gram-scale reaction and a further transformation of one of the products.

Polystyrene resin supported palladium(0) (Pd@PR) nanocomposite mediated regioselective synthesis of 4-aryl-1-alkyl/(2-haloalkyl)-1H-1,2,3-triazoles and their N-vinyl triazole derivatives from terminal alkynes

RSC Advances ◽  
2015 ◽  
Vol 5 (15) ◽  
pp. 11506-11514 ◽  
Author(s):  
Arun K. Shil ◽  
Sandeep Kumar ◽  
Saurabh Sharma ◽  
Abha Chaudhary ◽  
Pralay Das
Keyword(s):  
Regioselective Synthesis ◽  
Terminal Alkynes ◽  
One Pot ◽  
Triazole Derivatives ◽  
General Methodology ◽  
One Pot Synthesis ◽  
Supported Palladium ◽  
Polystyrene Resin

An efficient general methodology has been developed for sequential one-pot synthesis of 4-aryl-1-alkyl-1H-1,2,3-triazoles influenced by Pd@PR nanocomposite.

Synthesis of 1,4-Disubstituted 1H-1,2,3-Triazoles from 4-(1-Adamantyl)benzyl Azide through a 1,3-Dipolar Cycloaddition Reaction

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2685-2688
Author(s):  
Dahmane Tebbani ◽  
Artur Silva ◽  
Oussama Hocine
Keyword(s):  
Copper Catalyst ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
Triazole Derivatives

A series of new 1,4-disubstituted 1H-1,2,3-triazole derivatives were synthesized by an efficient copper-catalyzed 1,3-dipolar cyclo­addition reaction of 4-(1-adamantyl)benzyl azide with several terminal alkynes. The copper catalyst was used to provide 1,4-disubstituted 1,2,3-triazoles regioselectively in good yields.

scholarly journals Synthesis and Anti-Inflammatory Activity of New Alkyl-Substituted Phthalimide 1H-1,2,3-Triazole Derivatives

2012 ◽  
Vol 2012 ◽  
pp. 1-7 ◽  
Author(s):  
Shalom Pôrto de Oliveira Assis ◽  
Moara Targino da Silva ◽  
Ronaldo Nascimento de Oliveira ◽  
Vera Lúcia de Menezes Lima
Keyword(s):  
Cycloaddition Reaction ◽  
Inflammatory Activity ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
Triazole Derivatives ◽  
Inflammatory Agent ◽  
Anti Inflammatory ◽  
The Right

Four new 1,2,3-triazole phthalimide derivatives with a potent anti-inflammatory activity have been synthesized in the good yields by the 1,3-dipolar cycloaddition reaction fromN-(azido-alkyl)phthalimides and terminal alkynes. The anti-inflammatory activity was determined by injecting carrageenan through the plantar tissue of the right hind paw of Swiss white mice to produce inflammation. All the compounds3a–cand5a–cexhibited an important anti-inflammatory activity; the best activity was found for the compounds3band5c, which showed to be able to decrease by 69% and 56.2% carrageenan-induced edema in mice. These compounds may also offer a future promise as a new anti-inflammatory agent.

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