Efficient one-pot synthesis of propargylamines using zinc dust

Kantam, M. Lakshmi; Balasubrahmanyam, V.; Kumar, K. B. Shiva; Venkanna, Gopaladasu T.

doi:10.1016/j.tetlet.2007.08.020

Cited by 72 publications

(21 citation statements)

References 31 publications

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“…This is on account of the poisoning of the mesoporous catalyst by irreversible pore blocking and reduction of yields in subsequent trials. Most of the compounds thus formed are known: propargylamines a, [33] b, [33] d, [31] g, [8] h, [33] i, [26,41] j, [8] k, [33] l, [33] m, [20,27] n, [42,43] o, [31] p [28] and q [44] have been previously reported. The unknown products, e, c and f…”

Section: General Procedures For the Synthesis Of Propargylamines By Thmentioning

confidence: 99%

Copper(I)‐N₂S₂‐salen type complex covalently anchored onto MCM‐41 silica: an efficient and reusable catalyst for the A³‐coupling reaction toward propargylamines

Naeimi

Moradian

2013

Applied Organom Chemis

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The immobilization of copper complexes by covalent anchoring of the ligand on the surface of mesoporous MCM‐41 has been described. Bis[2‐(phenylthio)benzylidene]‐1,2‐ethylenediamine as a new N2S2 donor salen‐type ligand was covalently anchored onto nanopores of MCM‐41 coordinated with copper (I) halide. The organic–inorganic hybrid material was achieved readily using 3‐mercaptopropyltrimethoxysilane as a reactive surface modifier. 2‐Nitrobenzaldehyde was reacted smoothly with the thiol moieties in order to form functionalized nanoporous silica with carbaldehyde groups. The resulting supported organic moieties were converted to thiosalen ligand and coordinated with CuX (X = CN, Cl, Br, I). Characterization of the heterogeneous catalyst by X‐ray diffraction, N2 sorption, FT‐IR, diffuse reflectance UV‐visible and TGA techniques indicated successful grafting of the copper complex inside the nano‐channels of MCM‐41. The heterogenized catalyst was evaluated by the Mannich condensation reaction of aldehydes, amines and alkynes. In this reaction, the corresponding propargylamines were obtained as single products in good to excellent yields. Factors such as reaction temperature, solvent, catalyst loading, leaching and reusability of the catalyst also were discussed. The use of MCM‐41 as support permits an easier separation and recycles with only a marginal decrease in reactivity. Copyright © 2013 John Wiley & Sons, Ltd.

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Section: General Procedures For the Synthesis Of Propargylamines By Thmentioning

confidence: 99%

Copper(I)‐N₂S₂‐salen type complex covalently anchored onto MCM‐41 silica: an efficient and reusable catalyst for the A³‐coupling reaction toward propargylamines

Naeimi

Moradian

2013

Applied Organom Chemis

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“…Additionally, it is possible to modify the chemo‐, regio‐ and enantio‐selectivity of the catalyst. This reaction has been catalyzed by Cu, Au, Ag, Zn, Fe, Ni, Rh, Hg, In, Ir, Mn, Co, Bi, Cd . The homogenous catalysts do have some disadvantages, as they are difficult to separate from the reaction mixtures.…”

Section: Introductionmentioning

confidence: 99%

Carbon Nitride‐Supported Silver Nanoparticles: Microwave‐ Assisted Synthesis of Propargylamine and Oxidative C‐C Coupling Reaction

Patel

Vasava

2018

ChemistrySelect

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In the present study we have, synthesized silver nanoparticles supported on carbon nitride AgNPs@g‐C3N4 and investigated its catalytic aspects by using microwave. We found that silver nanoparticles supported on g‐C3N4 were highly active in the A3‐coupling reaction of (Aldehyde, secondary amine and terminal alkynes) for the synthesis of propargylamines with excellent yield up to 97% and in C−C coupling reaction of terminal alkynes for the synthesis of 1, 3‐diyne with excellent yield up to 98%. We have achieved excellent TON (72932), TOF (3636 min−1), E‐factor (0.27) and atom economy AE (94%). Reaction parameters like effect of catalyst quantity, effect of time and effect of temperature was deeply studied. The catalyst was characterized by SEM, HR‐TEM, EDX, XRD, ICP‐AES and IR.

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“…Different heterogeneous catalysts such as Ag I[16a] and Cu I[16b] compounds in ionic liquids, Zn dust,17 solid‐supported Au III ,18a Ag I ,18b–18d or Cu I ,18e–18h Fe 3 O 4 nanoparticles,19 or indium oxide nanoparticles20 have also been used for alkyne C–H activation.…”

Section: Introductionmentioning

confidence: 99%

A Facile Synthesis of 4,6,7,8,8a,9‐Hexahydropyrrolo[1,2‐a][1,2,3]triazolo[1,5‐d]pyrazines by a Three‐Component Coupling Reaction Followed by Intramolecular 1,3‐Dipolar Cycloaddition

et al. 2013

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A practical and efficient two‐step protocol for the synthesis of several new 4,6,7,8,8a,9‐hexahydropyrrolo[1,2‐a][1,2,3]triazolo[1,5‐d]pyrazines is described. The first step involves the AuBr3‐catalyzed three‐component coupling reaction of terminal alkynes, aldehydes, and amines under solvent‐free conditions to provide the requisite propargylamines. The reaction tolerates a high structural diversity, requires only short reaction times, gives high diastereoselectivities, and is environmentally benign. Furthermore, the propargylamine products undergo catalyst‐free intramolecular azide–alkyne [3 + 2] dipolar cycloaddition reactions to give the 4,6,7,8,8a,9‐hexahydropyrrolo[1,2‐a][1,2,3]triazolo[1,5‐d]pyrazines in excellent yields and with excellent diastereoselectivities.

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Efficient one-pot synthesis of propargylamines using zinc dust

Cited by 72 publications

References 31 publications

Copper(I)‐N₂S₂‐salen type complex covalently anchored onto MCM‐41 silica: an efficient and reusable catalyst for the A³‐coupling reaction toward propargylamines

Copper(I)‐N₂S₂‐salen type complex covalently anchored onto MCM‐41 silica: an efficient and reusable catalyst for the A³‐coupling reaction toward propargylamines

Carbon Nitride‐Supported Silver Nanoparticles: Microwave‐ Assisted Synthesis of Propargylamine and Oxidative C‐C Coupling Reaction

A Facile Synthesis of 4,6,7,8,8a,9‐Hexahydropyrrolo[1,2‐a][1,2,3]triazolo[1,5‐d]pyrazines by a Three‐Component Coupling Reaction Followed by Intramolecular 1,3‐Dipolar Cycloaddition

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Efficient one-pot synthesis of propargylamines using zinc dust

Cited by 72 publications

References 31 publications

Copper(I)‐N2S2‐salen type complex covalently anchored onto MCM‐41 silica: an efficient and reusable catalyst for the A3‐coupling reaction toward propargylamines

Copper(I)‐N2S2‐salen type complex covalently anchored onto MCM‐41 silica: an efficient and reusable catalyst for the A3‐coupling reaction toward propargylamines

Carbon Nitride‐Supported Silver Nanoparticles: Microwave‐ Assisted Synthesis of Propargylamine and Oxidative C‐C Coupling Reaction

A Facile Synthesis of 4,6,7,8,8a,9‐Hexahydropyrrolo[1,2‐a][1,2,3]triazolo[1,5‐d]pyr­azines by a Three‐Component Coupling Reaction Followed by Intramolecular 1,3‐Dipolar Cycloaddition

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Copper(I)‐N₂S₂‐salen type complex covalently anchored onto MCM‐41 silica: an efficient and reusable catalyst for the A³‐coupling reaction toward propargylamines

Copper(I)‐N₂S₂‐salen type complex covalently anchored onto MCM‐41 silica: an efficient and reusable catalyst for the A³‐coupling reaction toward propargylamines

A Facile Synthesis of 4,6,7,8,8a,9‐Hexahydropyrrolo[1,2‐a][1,2,3]triazolo[1,5‐d]pyrazines by a Three‐Component Coupling Reaction Followed by Intramolecular 1,3‐Dipolar Cycloaddition