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.

scholarly journals Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations

2016 ◽  
Vol 3 (9) ◽  
pp. 160090 ◽  
Author(s):  
Biswadip Banerji ◽  
K. Chandrasekhar ◽  
Sunil Kumar Killi ◽  
Sumit Kumar Pramanik ◽  
Pal Uttam ◽  
...  
Keyword(s):  
Density Functional ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Triazole Ring ◽  
Density Functional Theory Calculations ◽  
Dipolar Cycloaddition ◽  
Reaction Conditions ◽  
Functional Theory ◽  
Click Reactions ◽  
Counter Ions

‘Click reactions’ are the copper catalysed dipolar cycloaddition reaction of azides and alkynes to incorporate nitrogens into a cyclic hydrocarbon scaffold forming a triazole ring. Owing to its efficiency and versatility, this reaction and the products, triazole-containing heterocycles, have immense importance in medicinal chemistry. Copper is the only known catalyst to carry out this reaction, the mechanism of which remains unclear. We report here that the ‘click reactions’ can also be catalysed by silver halides in non-aqueous medium. It constitutes an alternative to the well-known CuAAC click reaction. The yield of the reaction varies on the type of counter ion present in the silver salt. This reaction exhibits significant features, such as high regioselectivity, mild reaction conditions, easy availability of substrates and reasonably good yields. In this communication, the findings of a new catalyst along with the effect of solvent and counter ions will help to decipher the still obscure mechanism of this important reaction.

scholarly journals Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4416
Author(s):  
Vasilichia Antoci ◽  
Costel Moldoveanu ◽  
Ramona Danac ◽  
Violeta Mangalagiu ◽  
Gheorghita Zbancioc
Keyword(s):  
Reaction Time ◽  
Comparative Study ◽  
Cycloaddition Reaction ◽  
Environmentally Friendly ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Thermal Heating ◽  
Dipolar Cycloadditions ◽  
Methyl Propiolate

We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained. Under conventional TH, the cycloaddition reaction of phthalazinium ylides with DMAD occurs to a mixture of inseparable partial and fully aromatized pyrrolophthalazine cycloadducts, while MW or US irradiation are leading only to fully aromatized compounds, with the reactions becoming selective. A feasible mechanism for formation of fully aromatized compounds is presented. Besides selectivity, it has to be noticed that the reaction setup under MW or US irradiation offer a number of other certain advantages: higher yields, decreasing of the amount of used solvent comparative with TH, decreasing of the reaction time from hours to minutes and decreasing of the consumed energy; consequently, these reactions could be considered environmentally friendly.

Stepwise π-extension of meso-alkylidenyl porphyrins through sequential 1,3-dipolar cycloaddition and redox reactions

2014 ◽  
Vol 50 (66) ◽  
pp. 9277-9280 ◽  
Author(s):  
Dowoo Park ◽  
Seung Doo Jeong ◽  
Masatoshi Ishida ◽  
Chang-Hee Lee
Keyword(s):  
Redox Reactions ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
High Yields

Novel pi-extended,meso-malonylidene porphyrins have been synthesized in high yields by 1,3-dipolar cycloaddition reaction with the azomethine ylide.

scholarly journals NaOH/PEG-400: An eloquent system for the synthesis of new thienyl benzo[b]1,4-diazepines

2020 ◽  
Vol 11 (4) ◽  
pp. 276-279
Author(s):  
Gajanan Gopinath Mandawad ◽  
Baseer Mubeen Shaikh ◽  
Santosh Subhash Chobe ◽  
Shankaraiah Guruvaiah Konda
Keyword(s):  
Polyethylene Glycol ◽  
Reaction Time ◽  
Present Method ◽  
Spectroscopic Methods ◽  
Reaction Conditions ◽  
Environment Friendly ◽  
Peg 400 ◽  
High Yields ◽  
Work Up

A simple and eloquent procedure for the synthesis of a new series of thienyl benzo[b]1,4-diazepines is reported. They were synthesized by the condensation of o-phenylenediamine (o-PDA) with distinct hetero chalcones using NaOH in polyethylene glycol (PEG-400) as green and alternative reaction solvent. The significances of this present method are shorter reaction time, easy work-up, high yields, and mild reaction conditions. Furthermore, this method is environment friendly and without use of an expensive catalyst. The all newly synthesized compounds are characterized by the spectroscopic methods.

scholarly journals "Click" chemistry as a tool to create novel biomaterials: a short review

2017 ◽  
Vol 1 (1) ◽  
pp. 22-34
Author(s):  
Mariana Barbosa ◽  
Cristina Martins ◽  
Paula Gomes
Keyword(s):  
Click Chemistry ◽  
Biomedical Applications ◽  
Recent Literature ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Polymeric Materials ◽  
Short Review ◽  
Dipolar Cycloaddition ◽  
Functionalization Of Polymers ◽  
Grafting Modification

In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 267-271 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Atiyeh Moafi ◽  
Behzad Jafari ◽  
Alexander Vilinger ◽  
Peter Langer
Keyword(s):  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
Relative Stereochemistry ◽  
High Yields

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

scholarly journals Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine

2020 ◽  
Vol 2020 ◽  
pp. 1-8
Author(s):  
Khadija Nabih ◽  
Mohamed Maatallah ◽  
Abdesselam Baouid ◽  
Abdellah Jarid
Keyword(s):  
Energy Barrier ◽  
Addition Reaction ◽  
Cycloaddition Reaction ◽  
Reaction Medium ◽  
Dft Method ◽  
High Energy ◽  
Dipolar Cycloaddition ◽  
Concerted Mechanism ◽  
Heat Released ◽  
Good Agreement

In this work, the mechanism and regio- and no-periselectivity of the 1,3-dipolar cycloaddition reaction of 2,4-dimethyl-3H-1,5-benzodiazepine with N-aryl-C-ethoxycarbonylnitrilimine have been studied using the DFT method at the B3LYP/6-31G(d) level of theory. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. The two C=N sites of 2,4-dimethyl-3H-1,5-benzodiazepine are easily reached by the dipole, and the energy barrier between the reagents and the transition states is too weak. The secondary barriers are traversed by the heat released in the reaction medium after the crossing of the first TS, which facilitates the addition reaction and does not require high energy. The obtained results of this study are in good agreement with experimental outcomes.

Application of the Palladium(0)-Catalyzed Ullmann Cross-Coupling Reaction in a Total Synthesis of (±)-Aspidospermidine and thus Representing an Approach to the Lower Hemisphere of the Binary Indole - Indoline Alkaloid Vinblastine

2005 ◽  
Vol 58 (10) ◽  
pp. 722 ◽  
Author(s):  
Martin G. Banwell ◽  
David W. Lupton ◽  
Anthony C. Willis
Keyword(s):  
Total Synthesis ◽  
Addition Reaction ◽  
Cycloaddition Reaction ◽  
Coupling Reaction ◽  
Dipolar Cycloaddition ◽  
Lower Hemisphere ◽  
Cross Coupling Reaction ◽  
Bicyclic System ◽  
Anti Cancer ◽  
Cancer Agent

As part of ongoing studies directed towards the construction of the anti-cancer agent vinblastine (1), the related but structurally less complex natural product aspidospermidine (3) has been synthesized. Two approaches to target 3 were pursued. In the first, which was unsuccessful, the amine-tethered enone 6 was prepared but this failed to engage in the pivotal intramolecular conjugate addition reaction to give the bicyclic system 5. In contrast, the related compound 46, incorporating tethered enone and azide moieties, engaged in an intramolecular 1,3-dipolar cycloaddition reaction to give, presumably via an intermediate triazoline, the isolable and ring-fused aziridine 47. This was then converted, over two steps, into the previously reported tetrahydrocarbazole 4. Application of established protocols to this last compound allowed for the installation of the E-ring of the title alkaloid 3 and completion of the total synthesis.

Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: direct access to 3,4,5-trisubstituted isoxazoles

2016 ◽  
Vol 14 (23) ◽  
pp. 5246-5250 ◽  
Author(s):  
Xiao Zhou ◽  
Xianhong Xu ◽  
Zhenyan Shi ◽  
Kun Liu ◽  
Hua Gao ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
High Yields

Enolate-mediated [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of β-functionalized ketones with nitrile oxides have been developed. This strategy could generate 3,4,5-trisubstituted isoxazole in high yields and regioselectivities.

scholarly journals Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry

2017 ◽  
Vol 82 (3) ◽  
pp. 241-251 ◽  
Author(s):  
Kothuri Kiran ◽  
Dongamanti Ashok ◽  
Boddu Rao ◽  
Madderla Sarasija ◽  
Alapati Rao
Keyword(s):  
Click Reaction ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Scavenging Activity ◽  
Bacterial Strains ◽  
Standard Drug ◽  
Mass Spectral ◽  
Nitric Oxide Radical

A series of novel bis(1,2,3-triazoles) derivatives 7a?m were synthesized by the 1,3-dipolar cycloaddition (click-reaction) of 1-methyl-3,5-bis(2- -(prop-2-yn-1-yloxy)phenyl)-4,5-dihydro-1H-pyrazole (5) with various aralkyl azides 6a?m in the presence of sodium ascorbate and copper sulphate with good yields. The required precursor 5 was synthesized by reacting (E)-1,3- -bis(2-hydroxyphenyl)prop-2-en-1-one (3) with methylhydrazine hydrate via 2,2?-(1-methyl-4,5-dihydro-1H-pyrazole-3,5-diyl)diphenol 4, followed by reaction with propargyl bromide. The homogeneity of all the newly synthesized compounds was checked by TLC. The IR, NMR, mass spectral data and elemental analysis were in accord with the assigned structure. The title compounds were evaluated for their antibacterial activity against various bacterial strains, i.e., Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis; compounds 7f?7h and 7j were found to be moderately active against the bacteria, when compared with that of the standard drug. Furthermore, the same library of compounds was evaluated for their antioxidant activity using the nitric oxide radical scavenging activity. The results of the study showed that compounds 7e?7h and 7k?7m showed good radical scavenging activity.

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