Azide-Enolate 1,3-Dipolar Cycloaddition as an Efficient Approach for the Synthesis of 1,5-Disubstituted 1,2,3-Triazoles from Alkyl/Aryl Azides and β-Ketophosphonates

2016 ◽  
Vol 2016 (4) ◽  
pp. 668-672 ◽  
Author(s):  
Davir González-Calderón ◽  
Aydeé Fuentes-Benítes ◽  
Eduardo Díaz-Torres ◽  
Carlos A. González-González ◽  
Carlos González-Romero
Keyword(s):  
Dipolar Cycloaddition ◽  
Aryl Azides ◽  
Alkyl Aryl ◽  
Efficient Approach

ChemInform Abstract: Azide-Enolate 1,3-Dipolar Cycloaddition as an Efficient Approach for the Synthesis of 1,5-Disubstituted 1,2,3-Triazoles from Alkyl/Aryl Azides and β-Ketophosphonates.

ChemInform ◽  
2016 ◽  
Vol 47 (25) ◽  
Author(s):  
Davir Gonzalez-Calderon ◽  
Aydee Fuentes-Benites ◽  
Eduardo Diaz-Torres ◽  
Carlos A. Gonzalez-Gonzalez ◽  
Carlos Gonzalez-Romero
Keyword(s):  
Dipolar Cycloaddition ◽  
Aryl Azides ◽  
Alkyl Aryl ◽  
Efficient Approach

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.

Novel synthesis of 1,5-disubstituted-1,2,3-triazolines catalysed by Zepto magnetic microspheres under the influence of a rotating magnetic field

2019 ◽  
Vol 97 (3) ◽  
pp. 163-168 ◽  
Author(s):  
Priyanka Sharma ◽  
Srinivasu V. Vallabhapurapu ◽  
Wei H. Ho ◽  
Nanjundaswamy M. Hemmaragala
Keyword(s):  
Magnetic Field ◽  
Magnetic Force ◽  
Rotating Magnetic Field ◽  
Magnetic Microspheres ◽  
The Novel ◽  
Aryl Azides ◽  
Alkyl Aryl ◽  
Novel Synthesis ◽  
Bead Diameter ◽  
Magnetic Poles

The novel reactor has been designed to perform chemical reactions under the influence of a magnetic field generated by alternating magnetic poles as a function of time. The system was successfully employed to synthesize a series of 1,5-disubstituted-1,2,3-triazolines via the regioselective [3 + 2] cycloaddition reactions between alkyl/aryl azides and nitroolefins catalysed by Zepto (para magnetic ultra-blue carboxy functionalized) microspheres (bead diameter 2.5 μm). All of the reactions went smoothly without any adverse effect on nitro, cyano, thienyl, hydroxy, halogens, and ether functions at 25 ± 2 °C and afforded 82%–99% pure products at a magnetic field of 18.99 mT and an exposure time of 180–240 min. The influence of the magnetic force exerted on the magnetic materials was found to enhance the catalytic activity of microspheres. The catalyst could easily be separated by simple centrifugation, which could be reused for at least 15 runs with no loss in activity.

Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: An efficient approach to novel P-stereogenic 1,2-diphosphine systems

2008 ◽  
pp. 5408 ◽  
Author(s):  
Nikolai Vinokurov ◽  
K. Michał Pietrusiewicz ◽  
Sławomir Frynas ◽  
Michael Wiebcke ◽  
Holger Butenschön
Keyword(s):  
Dipolar Cycloaddition ◽  
Efficient Approach

scholarly journals Synthesis of Novel Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

2013 ◽  
Vol 24 (2) ◽  
pp. 179-183 ◽  
Author(s):  
Bianca N. M. Silva ◽  
Bárbara V. Silva ◽  
Fernando C. Silva ◽  
Daniel T. G. Gonzaga ◽  
Vitor F. Ferreira ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Alkyl Aryl

A novel and efficient approach to mono-N-alkyl anilines via addition of grignard reagents to aryl azides

1999 ◽  
Vol 40 (47) ◽  
pp. 8305-8306 ◽  
Author(s):  
H.M. Sampath Kumar ◽  
B.V. Subba Reddy ◽  
S. Anjaneyulu ◽  
J.S. Yadav
Keyword(s):  
Grignard Reagents ◽  
Aryl Azides ◽  
Efficient Approach

Palladium-catalyzed C—O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones

2015 ◽  
Vol 64 (4) ◽  
pp. 859-863 ◽  
Author(s):  
O. V. Turova ◽  
V. G. Berezhnaya ◽  
E. V. Starodubtseva ◽  
V. A. Ferapontov ◽  
M. G. Vinogradov
Keyword(s):  
Alkyl Aryl ◽  
Efficient Approach ◽  
Palladium Catalyzed

Simple, stepwise and alternative syntheses of indolyl triazoles via Huisgen,s 1, 3-dipolar cycloaddition reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Ch. Venkata Ramana Reddy ◽  
G. Ganga Reddy
Keyword(s):  
Reaction Time ◽  
Addition Reaction ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Spectroscopic Methods ◽  
Aryl Azides ◽  
Simple Processing ◽  
High Yields

: A series of new 2-((1-((1-(4-methoxy-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)1H-indol-3-yl)me thylene)malononitrile derivatives were synthesized by the 1,3 dipolar cyclo addition reaction (click reaction) of 2-((1-(prop-2-yn-1-yl)-1H-indol-3-yl)methylene)malononitrile with different aryl azides in the presence of sodium ascorbate and copper sulphate in good yields. The advantages of this method are efficient, clean, high yields, easy workup procedures and shorter reaction time. These reactions are very facile giving products by simple processing that does not require purification by column chromatography. All the newly synthesized compounds were confirmed by spectroscopic methods.

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