Supported NHC-Benzimi@Cu Complex as a Magnetically Separable and Reusable Catalyst for the Multicomponent and Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Huisgen 1,3-Dipolar Cycloaddition

2021 ◽  
Author(s):  
Arvind Pawar ◽  
Shivanand Gajare ◽  
Ashutosh Jagdale ◽  
Sandip Patil ◽  
Wilson Chandane ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Reusable Catalyst ◽  
Cu Complex ◽  
Magnetically Separable ◽  
Click Synthesis

1,3-dipolar cycloaddition in the synthesis of glycoconjugates of natural chlorins and bacteriochlorins

2009 ◽  
Vol 13 (03) ◽  
pp. 336-345 ◽  
Author(s):  
Mikhail A. Grin ◽  
Ivan S. Lonin ◽  
Anna A. Lakhina ◽  
Elena S. Ol'shanskaya ◽  
Alexey I. Makarov ◽  
...  
Keyword(s):  
Triple Bond ◽  
Tautomeric Form ◽  
Click Reaction ◽  
Copper Cation ◽  
Water Soluble ◽  
Dipolar Cycloaddition ◽  
Nmr Studies ◽  
Metal Free ◽  
Cu Complex ◽  
Derivatives Of

Glucose-, galactose- and lactose-containing photosensitizers based on derivatives of chlorophyll a and bacteriochlorophyll a were synthesized with the use of [3+2] cycloaddition between sugar azides and triple bond derivatives of chlorins and bacteriochlorins. Unlike bacteriochlorin cycloimide, chlorin was detected to form a Cu -complex during the click reaction. An approach to the synthesis of metal-free glycosylated chlorins was developed with the use of "protection" by Zn 2+ cation and subsequent demetalation. It is based on the action of alkynyl chlorin e6 derivative Zn -complex, which is resistant to the substitution by copper cation. Bacteriochlorin p cycloimide conjugate with per-acetylated β-D-lactose was obtained and shown to become water-soluble after unblocking of the lactose hydroxy functions. NMR studies allowed for the elucidation of structure, tautomeric form and conformation of the obtained compounds.

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.

scholarly journals C–C and C–H coupling reactions by Fe3O4/KCC-1/APTPOSS supported palladium-salen-bridged ionic networks as a reusable catalyst

RSC Advances ◽  
2018 ◽  
Vol 8 (16) ◽  
pp. 8761-8769 ◽  
Author(s):  
Asadollah Hassankhani ◽  
Seyed Mohsen Sadeghzadeh ◽  
Rahele Zhiani
Keyword(s):  
Potential Application ◽  
Reusable Catalyst ◽  
Coupling Reactions ◽  
Supported Palladium ◽  
Magnetically Separable

This study investigates the potential application of an efficient, easily recoverable and reusable magnetically separable Fe3O4/KCC-1/APTPOSS nanoparticle-supported salen/Pd(ii) catalyst for C–C and C–H cross-couplings.

A polymer supported ascorbate functionalized task specific ionic liquid: an efficient reusable catalyst for 1,3-dipolar cycloaddition

RSC Advances ◽  
2015 ◽  
Vol 5 (27) ◽  
pp. 21396-21404 ◽  
Author(s):  
Jayavant D. Patil ◽  
Supriya A. Patil ◽  
Dattaprasad M. Pore
Keyword(s):  
Ionic Liquid ◽  
Dipolar Cycloaddition ◽  
Reusable Catalyst ◽  
Efficient Catalyst ◽  
Polymer Supported ◽  
Task Specific Ionic Liquid

In situ coalescence of copper on polymer supported ascorbate functionalized task specific ionic liquid, acts as an efficient catalyst for Huisgen 1,3 dipolar cycloaddition.

Nanoceria supported cobalt(0) nanoparticles: a magnetically separable and reusable catalyst in hydrogen generation from the hydrolysis of ammonia borane

2017 ◽  
Vol 41 (14) ◽  
pp. 6546-6552 ◽  
Author(s):  
Serdar Akbayrak ◽  
Oğuzcan Taneroğlu ◽  
Saim Özkar
Keyword(s):  
Hydrogen Generation ◽  
Ammonia Borane ◽  
Reusable Catalyst ◽  
Magnetically Separable ◽  
Hydrolysis Of

Co0/CeO2 is a magnetically separable and highly reusable catalyst in the hydrolysis of ammonia borane.

Nano-CuFe2O4 as a magnetically separable and reusable catalyst for the synthesis of diaryl/aryl alkyl sulfides via cross-coupling process under ligand-free conditions

2011 ◽  
Vol 9 (17) ◽  
pp. 5989 ◽  
Author(s):  
Kokkirala Swapna ◽  
Sabbavarapu Narayana Murthy ◽  
Mocharla Tarani Jyothi ◽  
Yadavalli Venkata Durga Nageswar
Keyword(s):  
Cross Coupling ◽  
Reusable Catalyst ◽  
Coupling Process ◽  
Ligand Free ◽  
Magnetically Separable

ChemInform Abstract: Ionic Polymer-Supported Copper(I): A Reusable Catalyst for Huisgen′s 1,3-Dipolar Cycloaddition.

ChemInform ◽  
2009 ◽  
Vol 40 (4) ◽  
Author(s):  
Uthaiwan Sirion ◽  
Yu Jin Bae ◽  
Byoung Se Lee ◽  
Dae Yoon Chi
Keyword(s):  
Dipolar Cycloaddition ◽  
Reusable Catalyst ◽  
Ionic Polymer ◽  
Polymer Supported

Ag nanoparticle immobilized mesoporous TiO 2 -cobalt ferrite nanocatalyst: A highly active, versatile, magnetically separable and reusable catalyst

2017 ◽  
Vol 94 ◽  
pp. 361-370 ◽  
Author(s):  
Barun Kumar Ghosh ◽  
Debabrata Moitra ◽  
Madhurya Chandel ◽  
Harshita Lulla ◽  
Narendra Nath Ghosh
Keyword(s):  
Cobalt Ferrite ◽  
Reusable Catalyst ◽  
Ag Nanoparticle ◽  
Highly Active ◽  
Magnetically Separable

scholarly journals Metal-Free Click Synthesis of Functional 1-Substituted-1,2,3-Triazoles

2019 ◽  
Author(s):  
Marie-Claire Giel ◽  
Christopher J. Smedley ◽  
Emily R. R. Mackie ◽  
Taijie Guo ◽  
Jiajia Dong ◽  
...  
Keyword(s):  
Click Reaction ◽  
Dipolar Cycloaddition ◽  
Chromatographic Purification ◽  
Metal Free ◽  
Organic Azides ◽  
Novel Method ◽  
Fluoride Salts ◽  
Sulfonyl Fluoride ◽  
Click Synthesis ◽  
Selection Of

The 1,2,3-triazole group is one of the most important connective linkers and functional aromatic heterocycles in modern chemistry. The boom in growth of, in particular, 1,4-disubstituted triazole products since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles, has been surprisingly more challenging. We report a straightforward and scalable click-protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene-surrogate, ethenesulfonyl fluoride (ESF). The transformation proceeds through a thermal 1,3-dipolar cycloaddition of the azide and ESF to give a sulfonyl fluoride substituted triazoline, that itself spontaneously aromatizes through formal loss of HF/SO<sub>2 </sub>to give the stable triazole products with excellent fidelity. The new click reaction tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield, and without need for additives or chromatographic purification. Further, under controlled conditions, the 1-substituted-1,2,3-triazole products undergo Michael reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts, demonstrating the versatility and orthogonal reactivity of ESF. The importance of this novel method is evidenced through the late-stage modification of several drugs and drug fragments, including the synthesis of a new improved derivative of the famous antibiotic, chloramphenicol.

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