A highly efficient and sustainable synthesis of dihydropyrano[2,3-<i>c</i>]pyrazoles using polystyrene-supported p-toluenesulfonic acid as reusable catalyst

Chaudhari, Mahendra A.; Gujar, Jitendra B.; Kawade, Deepak S.; Jogdand, Nivrutti R.; Shingare, Murlidhar S.

doi:10.1080/23312009.2015.1063830

Cited by 23 publications

(8 citation statements)

References 39 publications

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“…PTSA is typically the catalyst of choice for both methods, as it is low in cost, and soluble in water, alcohol and organic solvents. Other organic acids have been utilized, but PTSA remains a favorable green heterogeneous catalyst, as it is efficient and can be reused [88,89]. It is also non-oxidizing to butanol, not corrosive on reactors, and considered a weak acid, which makes the neutralization step simple when producing APGs [90].…”

Section: Alkyl Polyglucosides (Apgs)mentioning

confidence: 99%

A review on the synthesis of bio-based surfactants using green chemistry principles

2022

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Objectives With increasing awareness of the potential adverse impact of conventional surfactants on the environment and human health, there is mounting interest in the development of bio-based surfactants (which are deemed to be safer, more affordable, are in abundance, are biodegradable, biocompatible and possess scalability, mildness and performance in formulation) in personal care products. Method A comprehensive literature review around alkyl polyglucosides (APGs) and sucrose esters (SEs) as bio-based surfactants, through the lens of the 12 green chemistry principles was conducted. An overview of the use of bio-based surfactants in personal care products was also provided. Results Bio-based surfactants are derived primarily from natural sources (i.e. both the head and tail molecular group). One of the more common types of bio-based surfactants are those with carbohydrate head groups, where alkyl polyglucosides (APGs) and sucrose esters (SEs) lead this sub-category. As global regulations and user mandate for sustainability and safety increase, evidence to further support these bio-based surfactants as alternatives to their petrochemical counterparts is advantageous. Use of the green chemistry framework is a suitable way to do this. While many of the discussed principles are enforced industrially, others have only yet been applied at a laboratory scale or are not apparent in literature. Conclusion Many of the principles of green chemistry are currently used in the synthesis of APGs and SEs. These and other bio-based surfactants should, therefore, be considered suitable and sustainable alternatives to conventional surfactants. To further encourage the use of these novel surfactants, industry must make an effort to implement and improve the use of the remaining principles at a commercial level. Graphical abstract

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Section: Alkyl Polyglucosides (Apgs)mentioning

confidence: 99%

A review on the synthesis of bio-based surfactants using green chemistry principles

2022

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“…Heterogeneous catalysts can be immobilized on various supports such as graphene, polymers, magnetic nanoparticles, zeolite, carbon, mesoporous silica, and silica sol–gels 11 – 26 . In recent decades, polymer-based supports have been studied extensively due to their several specifications, well-controlled structure, and ease of functionalization 15 – 21 . For example, polystyrene (PS) is one of the extensively used polymers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a magnetic polystyrene-supported Cu(II)-containing heterocyclic complex as a magnetically separable and reusable catalyst for the preparation of N-sulfonyl-N-aryl tetrazoles

Nasrollahzadeh

Motahharifar

Pakzad

et al. 2023

Sci Rep

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In this work, a cost-effective, environmentally friendly, and convenient method for synthesizing a novel heterogeneous catalyst via modification of polystyrene using tetrazole-copper magnetic complex [Ps@Tet-Cu(II)@Fe3O4] has been successfully developed. The synthesized complex was analyzed using TEM (transmission electron microscopy), HRTEM (high resolution-transmission electron microscopy), STEM (scanning transmission electron microscopy), FFT (Fast Fourier transform), XRD (X-ray diffraction), FT-IR (Fourier transform-infrared spectroscopy), TG/DTG (Thermogravimetry and differential thermogravimetry), ICP-OES (Inductively coupled plasma-optical emission spectrometry), Vibrating sample magnetometer (VSM), EDS (energy dispersive X-ray spectroscopy), and elemental mapping. N-Sulfonyl-N-aryl tetrazoles were synthesized in high yields from N-sulfonyl-N-aryl cyanamides and sodium azide using Ps@Tet-Cu(II)@Fe3O4 nanocatalyst. The Ps@Tet-Cu(II)@Fe3O4 complex can be recycled and reused easily multiple times using an external magnet without significant loss of catalytic activity.

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“…Synthesis of dihydropyrano[2,3- c ]pyrazoles can be achieved by various methodologies. Several catalysts including trimethylamine [ 25 , 26 , 27 ], piperazine [ 28 ], piperidine [ 29 ], N -methylmorpholine [ 30 ], heteropolyacids [ 31 ], glycine [ 32 ], per-6-amino-β-cyclodextrin [ 33 ], Mg/Al hydrotalcite [ 34 ], nanosized magnesium oxide [ 35 ], L-proline [ 36 ], γ-alumina [ 37 ], sodium benzoate [ 38 ], Amberlyst A21 [ 39 ] and CTACl [ 40 ], [Bmim]BF 4 [ 41 ], PS-PTSA [ 42 ], urea [ 43 ] and ethanol and water (1:1) [ 44 ] are reported in the literature. Ionic liquids have gained importance as green solvent for organic transformations [ 45 , 46 , 47 ] due to their special properties, including good solvating capability, negligible vapor pressure, non-inflammable, ease of recyclability, controlled miscibility and high thermal stability [ 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

Nimbalkar¹,

Seijas

Vázquez-Tato

et al. 2017

Molecules

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A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles 5a–j were synthesized via one-pot, four-component condensation reactions of aryl aldehydes 1a–j, propanedinitrile (2), hydrazine hydrate (3) and ethyl acetoacetate (4) under solvent-free conditions. We report herein the use of the Brønsted acid ionic liquid (BAIL) triethylammonium hydrogen sulphate [Et3NH][HSO4] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2), breast cancer cell line(MDA-MB-231), leukemia cancer cell line (K-562) and cervical cancer cell line (HeLa). Compounds 5b, 5d, 5g, 5h and 5j exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed 5b and 5d as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and non-toxic nature.

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A highly efficient and sustainable synthesis of dihydropyrano[2,3-c]pyrazoles using polystyrene-supported p-toluenesulfonic acid as reusable catalyst

Cited by 23 publications

References 39 publications

A review on the synthesis of bio-based surfactants using green chemistry principles

A review on the synthesis of bio-based surfactants using green chemistry principles

Synthesis of a magnetic polystyrene-supported Cu(II)-containing heterocyclic complex as a magnetically separable and reusable catalyst for the preparation of N-sulfonyl-N-aryl tetrazoles

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

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