Synthesis of 1,5-Functionalized 1,2,3-Triazoles Using Ionic Liquid/Iron(III) Chloride as Efficient and Reusable Homogeneous Catalyst

Nino, Antonio De; Merino, Pedro; Algieri, Vincenzo; Nardi, Mónica; Gioia, Maria Luisa Di; Russo, Beatrice; Matteo, Antonio Tallarida; Maiuolo, Loredana

doi:10.20944/preprints201807.0620.v1

Cited by 16 publications

(12 citation statements)

References 16 publications

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“…In this regard, as the pharmaceutical industry is known to use a large amount of solvents to produce active pharmaceutical ingredient (API), most of the investigations are currently focusing on the replacement of hazardous conventional solvents with more sustainable alternatives such as water [32][33][34][35][36][37][38][39][40], supercritical fluids [41,42], ionic liquids [43][44][45][46][47][48][49][50] and solvents derived from biomass [51][52][53] Deep eutectic solvents (DES) are considered the green solvents of the 21 st century with tremendous applicability in all areas of the chemical industry [54]. They can be defined as a mixture of two or more compounds, that at certain molar ratios exhibit a high depression of the melting point becoming liquid at or near room temperature.…”

Section: Figure 2 Examples Of Important Drugs Containing Benzimidazomentioning

confidence: 99%

Green Synthesis of Privileged Benzimidazole Scaffolds using Active Deep Eutectic Solvent

Gioia

Cassano

Costanzo

et al. 2019

Preprint

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The exploitation and use of alternative synthetic methods, in the face of classical procedures that do not conform to the ethics of Green Chemistry, represent an ever present problem in pharmaceutical industry. The procedures for the synthesis of benzimidazoles have become a focus in synthetic organic chemistry, as they are building blocks of strong interest for the development of compounds with pharmacological activity. Various benzimidazole derivatives exhibit important activities such as antimicrobial, antiviral, anti-inflammatory and analgesic and some of the already synthesized compounds have found very strong application in medicine praxis. Here we report a selective and sustainable method for the synthesis of 1,2-disubstituted or 2-substituted benzimidazoles, starting from o-phenylenediamine in the presence of different aldehydes. The use of deep eutectic solvent (DES) both as reaction medium and reagent without any external solvent provides advantages in terms of yields as well as in the work up procedure of the reaction.

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Section: Figure 2 Examples Of Important Drugs Containing Benzimidazomentioning

confidence: 99%

Green Synthesis of Privileged Benzimidazole Scaffolds using Active Deep Eutectic Solvent

Gioia

Cassano

Costanzo

et al. 2019

Preprint

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“…For these reasons, in recent years, synthetic procedures alternative to classical synthesis of substituted triazoles were proposed. In particular, in 2018, an efficient and reusable homogeneous catalyst consisting of ionic liquid/iron(III) chloride was applied in synthesis of 1,5-disubstituted 1,2,3-triazoles 24a-n, isolating the final products in considerable yields, high regioselectivity, furnishing only the 1,5-disubstituted substrate, and very short reaction time (Scheme 4) [37]. The synthetic process involves an eliminative azide-olefin cycloaddition (EAOC) reaction between nitroolefins 23a-n, excellent dipolarophiles to synthesize triazoles due to electronwithdrawing nitro group, and substituted azides 22 as dipoles.…”

Section: Synthesis Of Triazole Derivativesmentioning

confidence: 99%

Recent Developments on 1,3-Dipolar Cycloaddition Reactions by Catalysis in Green Solvents

et al. 2020

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The use of eco-compatible synthetic procedures in organic reactions and, in particular, in 1,3-dipolar cycloaddition reactions, has recently received a great deal of attention and considerable progress has been achieved in this area in the last years. This review summarizes the approaches currently employed to synthesize heterocyclic compounds by catalyzed 1,3-dipolar cycloadditions in green solvents in the last six years. Our choice to do a selection of the literature from 2014 to 2019 was made considering the absence of a recent review about this period, to our knowledge. Several examples to construct heterocycles by 1,3-dipolar cycloadditions will be discussed in this work subdivided in function of the most important class of non-conventional and green solvents, i.e., ionic liquids (ILs), deep eutectic solvents (DES), and water.

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“…Ionic liquids (ILs) are a class of organic salts whose melting temperature falls below the conventional limit of 100°C. Nowadays, due to their low vapor pressure and other peculiar characteristics, they are widely employed in organic synthesis as solvents so-called green, [121][122][123][124] but also used for other applications, such as industrial, pharmacology, bio-medicine, nanotechnology, etc. [125][126][127] Generally, amphiphilic ionic liquids are structures with a small hydrophilic head, generally represented by an imidazolium cation, and one or more hydrophobic moieties present on the backbone of the heterocycle.…”

Section: Amphiphilic Ionic Liquidsmentioning

confidence: 99%

Amphiphiles-metals interactions for applications in modern technologies: recent developments and future perspectives

Maiuolo¹,

Calandra²,

Lombardo³

et al. 2020

Rev.Roum.Chim.

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Amphiphiles play a pivotal role in the area of self-assembled structures and interesting additional features can be obtained if metal ions are involved. In this ambit, the development of smart materials benefits from the availability of stimuli-responsive supramolecular amphiphile assemblies where the disassembly back-processes has an inherently basic role providing reversible switching particularly useful in novel approaches and applications. In this tutorial review the basic concepts on self-assembly of traditional and novel amphiphilic molecules with metals are summarized and the more recent concepts of supramolecular assembly are presented. The aim of this contribution is to furnish to the reader a panoramic view of this exciting problematic clarifying what is meant with the concept of complexity and how the rich world of amphiphilic molecules is employed with metals for obtaining complex nanostructure-based systems with novel characteristics for applications in nanotechnology.

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Synthesis of 1,5-Functionalized 1,2,3-Triazoles Using Ionic Liquid/Iron(III) Chloride as Efficient and Reusable Homogeneous Catalyst

Cited by 16 publications

References 16 publications

Green Synthesis of Privileged Benzimidazole Scaffolds using Active Deep Eutectic Solvent

Green Synthesis of Privileged Benzimidazole Scaffolds using Active Deep Eutectic Solvent

Recent Developments on 1,3-Dipolar Cycloaddition Reactions by Catalysis in Green Solvents

Amphiphiles-metals interactions for applications in modern technologies: recent developments and future perspectives

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