Basic Ionic Liquid [bmIm]OH–Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes

Kaki, Venkata Rao; Akkinepalli, Raghuram Rao; Deb, Pran Kishore; Pichika, Mallikarjuna Rao

doi:10.1080/00397911.2014.951898

Cited by 20 publications

(10 citation statements)

References 24 publications

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“…All reagents and beginning compounds were provided by Fluka and Merck and were utilized without extra purification. All of the synthesized products were well known and characterized by comparison of their chemical and physical data to the literature . Melting points were obtained on a Bumstead electrothermal 9200 apparatus.…”

Section: Methodsmentioning

confidence: 99%

“…In the category of heterogeneous solid base catalysis, catalyst may function as a base toward reactants which ordinarily behave as acids either by abstraction of a proton from the reactants (Boensted base) or by donation of an electron pair to the reagents (Lewis base) to form anionic intermediates which undergo catalytic cycle . Recently, we examined the catalytic efficacy of ZnO, ZnO/nanoclinoptilolite and ZnFe 2 O 4 in the preparation of substituted 2‐aminothiophenes …”

Section: Introductionmentioning

confidence: 99%

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Ethylene diamine grafted nanoporous UiO‐66 as an efficient basic catalyst in the multi‐component synthesis of 2‐aminithiophenes

Erfaninia

Tayebee

Dušek

et al. 2018

Applied Organom Chemis

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This study demonstrates ED-UiO-66 as a novel and effective solid nanoporous basic catalyst prepared through the amine grafting onto the pores of UiO-66. The manufactured nanoparticles were identified by FT-IR, XRD, TGA, FESEM, TEM, CHN and BET and the characterization results certified formation of a single phase nanoporous substance with the medium grain size less than 90 nm. The synthesized material was employed as an efficient catalyst for the preparation of 2-aminotiophenes through the Gewald method. This thermochemically stable nanocatalyst was environmentally safe, reusable and economic. Therefore, this methodology can be simply extended for industrial goals.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ethylene diamine grafted nanoporous UiO‐66 as an efficient basic catalyst in the multi‐component synthesis of 2‐aminithiophenes

Erfaninia

Tayebee

Dušek

et al. 2018

Applied Organom Chemis

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“…The progress of the reactions was shown by thin‐layer chromatography (TLC). All the synthesized 2‐aminothiophenes were distinguished by comparison of their physical and spectral information with those already announced …”

Section: Methodsmentioning

confidence: 99%

Preparation of magnetically recyclable ZnFe₂O₄ nanoparticles by easy single‐step co‐precipitation method and their catalytic performance in the synthesis of 2‐aminothiophenes

Erfaninia

Tayebee

Foletto

et al. 2017

Applied Organom Chemis

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In this work, a new synthetic route for the preparation of ZnFe2O4 nanoparticles through the chemical co‐precipitation using Fe2+ and Fe3+ ions in an alkaline solution was developed. The synthesized nanoparticles were characterized by XRD, FTIR, SEM, ICP‐MS, DRS, TGA, VSM and elemental analysis. Characterization results confirmed the formation of single ZnFe2O4 phase, with an average particle size of 40 nm and a high saturation magnetization of 34 emu g−1. The prepared material was employed as a catalyst for the synthesis of 2‐aminotiophene derivatives through the Gewald reaction. This thermally and chemically stable nanocatalyst is environmentally benign, economical and reusable which can be easily recovered using an external magnet. Therefore, it appears that this methodology can be simply extended for industrial purposes.

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“…In recent years, room‐temperature ionic liquids (RTILs) have attracted increasing interest as green and reusable reaction media . The Gewald reaction has been effectively performed in ionic liquids under solvent‐free conditions, catalysed by ethylenediammonium diacetate (EDDA) .…”

Section: Gewald Reaction Modificationsmentioning

confidence: 99%

The Gewald reaction in dye chemistry

Sabnis¹

2016

Coloration Technology

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This review presents the most elegant and promising set of synthetic routes for the synthesis of 2‐aminothiophenes by the Gewald reaction. This reaction has applications in several applied fields, such as pharmaceuticals/biomedicine, agrochemicals, carbohydrate conjugates, sugar cane ripeners, peptide analogues, dyestuffs, and electronic materials; however, the present review will focus on the use of Gewald chemistry in the synthesis of conventional and functional colourants. The Gewald reaction produces 2‐aminothiophene, which is a key intermediate for the diazotisation reaction and for the synthesis of azo dyes, and thus opened the door for new dye chemistry. The reaction produces electron‐withdrawing groups such as CN, COOEt, COOMe, CONH2, and COPh in the 3‐ and/or 5‐position, resulting in bathochromic shifts for the deeper colours of the dyes. The review further reveals the importance of this reaction in the synthesis of azo dyes, fluorescent dyes (coumarin dyes, styryl dyes, thieno[2,3‐d]pyrimidine dyes, bithiophene dyes), thiophene analogues of phthalocyanines, and fluorescent whitening agents.

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Basic Ionic Liquid [bmIm]OH–Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes

Cited by 20 publications

References 24 publications

Ethylene diamine grafted nanoporous UiO‐66 as an efficient basic catalyst in the multi‐component synthesis of 2‐aminithiophenes

Ethylene diamine grafted nanoporous UiO‐66 as an efficient basic catalyst in the multi‐component synthesis of 2‐aminithiophenes

Preparation of magnetically recyclable ZnFe₂O₄ nanoparticles by easy single‐step co‐precipitation method and their catalytic performance in the synthesis of 2‐aminothiophenes

The Gewald reaction in dye chemistry

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Basic Ionic Liquid [bmIm]OH–Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes

Cited by 20 publications

References 24 publications

Ethylene diamine grafted nanoporous UiO‐66 as an efficient basic catalyst in the multi‐component synthesis of 2‐aminithiophenes

Ethylene diamine grafted nanoporous UiO‐66 as an efficient basic catalyst in the multi‐component synthesis of 2‐aminithiophenes

Preparation of magnetically recyclable ZnFe2O4 nanoparticles by easy single‐step co‐precipitation method and their catalytic performance in the synthesis of 2‐aminothiophenes

The Gewald reaction in dye chemistry

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Product

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About

Preparation of magnetically recyclable ZnFe₂O₄ nanoparticles by easy single‐step co‐precipitation method and their catalytic performance in the synthesis of 2‐aminothiophenes