Sustainable and selective synthesis of benzimidazole scaffolds using deep eutectic solvents

Shaibuna, M.; Hiba, K.; Shebitha, A.M.; Kuniyil, Muhammed Jeneesh Kariyottu; mole, P.B. Sherly; Sreekumar, K.

doi:10.1016/j.crgsc.2022.100285

Cited by 13 publications

(22 citation statements)

References 50 publications

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“…This was followed by straightforward work-up procedures that included the removal of solvent under reduced pressure, extraction, and solvent evaporation. Finally, the pure products were obtained after purifying through column chromatography, which was followed by the spectroscopic analysis of the pure compounds using 1 H NMR, 13 C NMR, and IR and high resolution mass (MS) spectroscopy.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…Unless otherwise noted all standard chemicals and solvents were used as purchased from commercial vendors without further purification. Using a Bruker DRX400 spectrometer, we were able to capture 1 H NMR (at 400 MHz) and 13 C NMR (at 100 MHz). Relative to the internal solvent peak, chemical shifts are reported in parts per million (ppm).…”

Section: Accepted Manuscriptmentioning

confidence: 99%

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One-Pot Telescopic Approach to Synthesize Disubstituted Benzimidazoles in Deep Eutectic Solvent

Das¹,

Chanda²

2023

Synthesis

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An ongoing challenge in the pharmaceutical sector is the need to find and implement novel synthetic approaches because traditional methods sometimes violate the principles of green chemistry. While benzimidazoles are of great importance as building blocks for the creation of molecules having pharmacological activity, the methods for their sustainable synthesis have been a challenge for organic synthesis. Herein, we have carried out a one-pot telescopic approach to synthesis disubstituted benzimidazole derivatives in a Deep Eutectic Solvent (DES) medium to investigate an alternate synthetic technique. Starting with methyl 4-fluoro-3-nitrobenzoate, SNAr reaction, reduction, and cyclization were performed with choline chloride/glycerol/H2O as DES medium which gave the best performance out of the five DESs. We report the synthesis of disubstituted benzimidazoles via one-pot telescopic approach.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Section: Accepted Manuscriptmentioning

confidence: 99%

One-Pot Telescopic Approach to Synthesize Disubstituted Benzimidazoles in Deep Eutectic Solvent

Das¹,

Chanda²

2023

Synthesis

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“…The higher acidity and lower viscosity of DES 1 was also favorable for its activity as an efficient catalyst for the synthesis of 2substituted benzimidazoles at room temperature (Scheme 39). 209 Scheme 34 Synthesis of 1-amidoalkyl naphthols (a) and polyhydroquinolines (b) using DES.…”

Section: Des As Catalyst/solvent For Organic Reactionsmentioning

confidence: 99%

“…The higher acidity and lower viscosity of DES 1 was also favorable for its activity as an efficient catalyst for the synthesis of 2-substituted benzimidazoles at room temperature (Scheme 39). 209 This method showed interesting characteristics such as the easy preparation of the catalyst, high product yield, simple reaction procedure, and the reusability of the catalyst.…”

Section: Applications Of Hydrophilic Dess In Various Organic Reactionsmentioning

confidence: 99%

Neoteric deep eutectic solvents: history, recent developments, and catalytic applications

Shaibuna

Theresa

2022

Soft Matter

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“…However, the synthesis of benzimidazole derivatives was far more efficient in the mixture ZrOCl 2 .8H 2 O:urea (1:5), which was achieved by the reaction of arene-1,2-diamine with aromatic aldehydes. The main reasons behind the good results obtained with this DES are the higher acidity and lower viscosity of this mixture compared with their ethylene glycol or glycerol HBD analogues ( Table 2 , entry 12) [ 44 ].…”

Section: Cyclization Reactionsmentioning

confidence: 99%

Deep Eutectic Solvents as à-la-Carte Medium for Transition-Metal-Catalyzed Organic Processes

Marset

Guillena

2022

Molecules

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Our society is facing a tremendous challenge to become more sustainable in every sphere of life. Regarding the chemical industry, one of the most significant issues to be addressed is the use of volatile organic compounds (VOCs) as solvents because they are petrol-derived and most of them are toxic and flammable. Among the possible solutions, deep eutectic solvents (DESs) have emerged as sustainable alternatives to VOCs in organic catalyzed transformations and other fields. The advantages of these new reaction media are not only related to their more benign physical and chemical properties and, for most of them, their renewable sources but also due to the possibility of being recycled after their use, increasing the sustainability of the catalyzed process in which they are involved. However, their use as media in catalytic transformations introduces new challenges regarding the compatibility and activity of known catalysts. Therefore, designed catalysts and “à-la-carte” DESs systems have been developed to overcome this problem, to maximize the reaction outcomes and to allow the recyclability of the catalyst/media system. Over the last decade, the popularity of these solvents has steadily increased, with several examples of efficient metal-catalyzed organic transformations, showing the efficiency of the catalysts/DES system, compared to the related transformations carried out in VOCs. Additionally, due to the inherent properties of the DES, unknown transformations can be carried out using the appropriated catalyst/DES system. All these examples of sustainable catalytic processes are compiled in this review.

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Sustainable and selective synthesis of benzimidazole scaffolds using deep eutectic solvents

Cited by 13 publications

References 50 publications

One-Pot Telescopic Approach to Synthesize Disubstituted Benzimidazoles in Deep Eutectic Solvent

One-Pot Telescopic Approach to Synthesize Disubstituted Benzimidazoles in Deep Eutectic Solvent

Neoteric deep eutectic solvents: history, recent developments, and catalytic applications

Deep Eutectic Solvents as à-la-Carte Medium for Transition-Metal-Catalyzed Organic Processes

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Sustainable and selective synthesis of benzimidazole scaffolds using deep eutectic solvents

Cited by 13 publications

References 50 publications

One-Pot Telescopic Approach to Synthesize Disubstituted Benz­imidazoles in Deep Eutectic Solvent

One-Pot Telescopic Approach to Synthesize Disubstituted Benz­imidazoles in Deep Eutectic Solvent

Neoteric deep eutectic solvents: history, recent developments, and catalytic applications

Deep Eutectic Solvents as à-la-Carte Medium for Transition-Metal-Catalyzed Organic Processes

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Product

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One-Pot Telescopic Approach to Synthesize Disubstituted Benzimidazoles in Deep Eutectic Solvent

One-Pot Telescopic Approach to Synthesize Disubstituted Benzimidazoles in Deep Eutectic Solvent