Energy efficient Pfitzinger reaction: a novel strategy using a surfactant catalyst

More, Priyanka A.; Shankarling, Ganapati S.

doi:10.1039/c7nj01937h

Cited by 13 publications

(9 citation statements)

References 24 publications

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“…It is pertinent to note, in terms of energy savings (energy supplied in kJ per mass of product), that sonication saved more than 78% energy with respect to the nonirradiated procedure. 89 A similar effect to that of surfactants on solvent’s surface tension can be obtained by hydrotropes in aqueous solution. The term hydrotrope denotes a nonmicelle forming substance, i.e., compounds that do not have a critical concentration above which self-aggregation takes place, while increasing the solubility of hydrophobic compounds.…”

Section: Sonochemical Reactivity: Convergent and Divergent Pathwaysmentioning

confidence: 79%

Organic Sonochemistry: A Chemist’s Timely Perspective on Mechanisms and Reactivity

2021

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Sonochemistry, the use of sound waves, usually within the ultrasonic range (>20 kHz), to boost or alter chemical properties and reactivity constitutes a long-standing and sustainable technique that has, however, received less attention than other activation protocols despite affordable setups. Even if unnecessary to underline the impact of ultrasound-based strategies in a broad range of chemical and biological applications, there is considerable misunderstanding and pitfalls regarding the interpretation of cavitational effects and the actual role played by the acoustic field. In this Perspective, with an eye on mechanisms in particular, we discuss the potentiality of sonochemistry in synthetic organic chemistry through selected examples of past and recent developments. Such examples illustrate specific controlling effects and working rules. Looking back at the past while looking forward to advancing the field, some essentials of sonochemical activation will be distilled.

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Section: Sonochemical Reactivity: Convergent and Divergent Pathwaysmentioning

confidence: 79%

Organic Sonochemistry: A Chemist’s Timely Perspective on Mechanisms and Reactivity

2021

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“…[123] Recently, Elias et al have reported a simple, efficient synthesis of quinolines (134) utilizing a hydrogen-Scheme 42. Synthesis of quinoline (128) using aniline (126) and acetaphenone (127). borrowing strategy as a greener option in chemical transformations from alcohols or ketones (132) and 2-aminobenzyl alcohols (133, Table 7, Entry 2) by using the water soluble [Ru(8-AQ)Cl(p-cym.)]…”

Section: Using 2-amino Benzylalcoholmentioning

confidence: 99%

“…Balaraman et al have devised technique for the novel and efficient synthetic protocols for the synthesis of quinolines (121) via rhodium-catalyzed CÀ H activation of substituted aniline (119) with methyl propiolate (120, Scheme 40) using cyclooctadiene rhodium chloride dimer [Rh(cod)Cl] 2 as catalysts and bis(diphenylphosphino)methane (dppm) as ligand. [119] The reaction proceeded through electrophilic metalation of 119 126), followed by carbonylation using paraformaldehyde and subsequential cyclization from methyl ketones (127) for the synthesis of quinolines having wide functional group tolerance in good to moderate yields (Scheme 42). [121]…”

Section: Using Alkynementioning

confidence: 99%

“…Shankarling and More have investigated an ecologically friendly way for the Pfitzinger reaction to synthesize quinoline‐4‐carboxylic acids ( 137 ) by utilizing a reusable basic surfactant, cetyltrimethylammonium ammonium hydroxide (CTAOH) in catalytic amount in water under the ultrasonic irradiation (Scheme 44). [127] The use of CTAOH have increased the solubility of isatin ( 135 ) and acetophenones ( 136 ) under aqueous conditions by trapping these substrates through the formation of micelles. The methodology involving the use of ultrasonic conditions have enabled more than 78 % of energy as compared to the conventional methods.…”

Section: Introductionmentioning

confidence: 99%

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Environmentally Benign Approaches towards the Synthesis of Quinolines

Kumar

Dhameliya²,

Sharma

et al. 2022

ChemistrySelect

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Greener and sustainable synthetic strategies have been evolving as the demanding domain of organic transformations during the last decade. The division of an environmentally benign methodology to construct bioactive heterocyclic scaffolds has always been a perpetual subject of interests for medicinal and synthetic chemists. Thus, the newer and novel synthetic methodologies of quinoline have drawn the attention of synthetic organic or medicinal chemists as evident from the growing numbers of publications. The current review focuses on some of the notable synthetic methodologies carried out in the last decade with the inherent objective to attain sustainability towards the synthesis. The key aspects of the review would include to highlight sustainable and environmentally benign approaches like the solvent‐free reactions, use of alternate reaction media (e. g., water, fluorous alcohols, polyethylene glycols, and ionic liquids), and alternate modes of synthesis such as microwave‐assisted synthesis and flow reactions, nano‐catalysts, etc.

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“…However, several of its derivatives have numerous applications such as pharmaceutical preparations [1], agricultural chemistry [2], materials and dyes [3], as well as in medicine. Recently, the nucleus of quinoline and plenty of its derivatives grasped interest to chemists and biologists owing to their many and necessary applications within the field of medicine as a number of them are used as antituberculosis [1,4,5], antimalarial [6], anticancer [7], antibiotic [8], hypotensive, antiviral [1], antioxidant [9], and antifungal [10]. Given the wide importance of quinoline derivatives, it is absolutely necessary to shed light on them during this analysis.…”

Section: Introductionmentioning

confidence: 99%

Quinoline-Based Materials: Spectroscopic Investigations as well as DFT and TD-DFT Calculations

Sakr

El‐Daly

Ebeid

et al. 2022

Journal of Chemistry

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Quinoline derivatives such as 15,15-difluoro-[1,3,2] diaazaborininodiquinoline (DDP) and 15,15-difluoro-[1,3,2] diaazaborininodiquinoline acetonitrile (DDPA) have a range of biological and medical activities. So, it is vital to shed light on these compounds in terms of their optical properties supported by quantum calculations. The absorption and emission spectra of studied compounds were measured within the laboratory, whereas the quantum calculations were performed utilizing the density functional theory (DFT) calculations. Additionally, the time-dependent density functional theory (TD-DFT) was applied for the comparison of some sensible results with the theoretical ones. The molecular structures of these compounds were presented via applying chemical analysis techniques. The electronic absorption spectra of DDP and DDPA molecular structures were monitored through an experiment in hosts such as carbon tetrachloride (CCl4), chloroform (CHCl3), methylene dichloride (CH2Cl2), acetone, and dimethyl sulfoxide (DMSO). Also, the influence of pH on the absorption spectra of the DDP molecule was studied. The molecular structures of these quinoline derivatives have been optimized via utilizing the B3LYP/6-31G (d) level of theory. The electronic absorption and emission spectra of the DDP compound in gas, THF, and DMSO have been calculated utilizing TD-DFT at the CAM-B3LYP/6-31G ++(d, p) level.

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Energy efficient Pfitzinger reaction: a novel strategy using a surfactant catalyst

Abstract: A novel ultrasound assisted synthetic route catalysed by a surfactant for the synthesis of quinolone-4-carboxylic acid.

Cited by 13 publications

References 24 publications

Organic Sonochemistry: A Chemist’s Timely Perspective on Mechanisms and Reactivity

Organic Sonochemistry: A Chemist’s Timely Perspective on Mechanisms and Reactivity

Environmentally Benign Approaches towards the Synthesis of Quinolines

Quinoline-Based Materials: Spectroscopic Investigations as well as DFT and TD-DFT Calculations

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