1,3-Dipolar Cycloaddition of Organic Azides to Alkynes by a Dicopper-Substituted Silicotungstate

2008 ◽  
Vol 130 (46) ◽  
pp. 15304-15310 ◽  
Author(s):  
Keigo Kamata ◽  
Yoshinao Nakagawa ◽  
Kazuya Yamaguchi ◽  
Noritaka Mizuno
Keyword(s):  
Dipolar Cycloaddition ◽  
Organic Azides

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.

scholarly journals Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides

2016 ◽  
Vol 374 (2) ◽  
Author(s):  
Jan Dommerholt ◽  
Floris P. J. T. Rutjes ◽  
Floris L. van Delft
Keyword(s):  
Dipolar Cycloaddition ◽  
Organic Azides

Carbon nanotube–copper ferrite-catalyzed aqueous 1,3-dipolar cycloaddition ofin situ-generated organic azides with alkynes

2018 ◽  
Vol 54 (29) ◽  
pp. 3644-3647 ◽  
Author(s):  
Praveen Prakash ◽  
Ramar Arun Kumar ◽  
Frédéric Miserque ◽  
Valérie Geertsen ◽  
Edmond Gravel ◽  
...  
Keyword(s):  
Carbon Nanotubes ◽  
Carbon Nanotube ◽  
Ferrite Nanoparticles ◽  
Dipolar Cycloaddition ◽  
Copper Ferrite ◽  
Organic Azides

A novel nanohybrid catalyst was developed by assembling copper ferrite nanoparticles on carbon nanotubes.

scholarly journals Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

2018 ◽  
Vol 14 ◽  
pp. 2689-2697 ◽  
Author(s):  
Robby Vroemans ◽  
Yenthel Verhaegen ◽  
My Tran Thi Dieu ◽  
Wim Dehaen
Keyword(s):  
Multicomponent Reaction ◽  
Mechanochemical Synthesis ◽  
Solvent Free ◽  
Viable Alternative ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Biologically Relevant ◽  
Metal Free ◽  
Organic Azides ◽  
Solvent Free Conditions

A new metal-free one-pot three-component procedure towards fully substituted triazolochromenes has been developed, starting from commercially available materials. Salicylaldehydes and nitroalkenes were reacted under solvent-free conditions, followed by a 1,3-dipolar cycloaddition of the intermediate 3-nitro-2H-chromenes with organic azides in a one-pot two-step sequence. The triazolochromenes were formed with complete regioselectivity and new biologically relevant structures were synthesized via extension of the developed procedure and via postfunctionalization. The mechanochemical synthesis was carried out for several salicylaldehydes and gave a clear improvement in the yield of the corresponding triazolochromenes and consequently showed to be a viable alternative for solid salicylaldehydes.

Regioselectivity in the 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides and Organic Azides with Bromocarbazole-1,4-diones.

ChemInform ◽  
2007 ◽  
Vol 38 (24) ◽  
Author(s):  
Muriel Compain-Batissou ◽  
Jacques Gentili ◽  
Nadia Walchshofer ◽  
Monique Domard ◽  
Bernard Fenet ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
Organic Azides

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.

scholarly journals Synthesis of a Novel Series of Phosphonate-Functionalized 1,2,3-Triazoles as Potential Candidates for Allosteric Modulation of α7 Nicotinic Acetylcholine Receptors

Proceedings ◽  
2018 ◽  
Vol 9 (1) ◽  
pp. 35
Author(s):  
Santiago A. Stabile ◽  
Cristian Vitale
Keyword(s):  
Nicotinic Acetylcholine Receptors ◽  
Acetylcholine Receptors ◽  
Dipolar Cycloaddition ◽  
Nicotinic Acetylcholine ◽  
Organic Azides ◽  
Bivalent Cations ◽  
Α7 Nachr ◽  
Α7 Nicotinic Acetylcholine Receptors ◽  
Allosteric Sites ◽  
Potential Activity

Nicotinic acetylcholine receptors (nAChR) are ligand-gated ion channels formed by the assembly of five subunits. Receptor activity could be subjected to both positive and negative modulation at allosteric sites by endogenous neurotransmitters as well as synthetic ligands such as steroids, bivalent cations, alcohols, and a range of drugs. The subtype of α7 nAChR has been considered a potential therapeutic target for Alzheimer’s disease, schizophrenia and other neurological and psychiatric disorders. In this work we present the synthesis of a novel series of phosphonate-functionalized 1,4-disubstituted 1,2,3-triazoles with potential activity over α7 AChR. These compounds were synthetized through the copper-catalyzed Huisgen 1,3-dipolar cycloaddition of organic azides and alkynes. Copper nanoparticles (CuNPs) immobilized on different supports were prepared using the CuCl2-Li-DTBB reducing system previously reported by our group.

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