Chitosan-SO3H: an efficient, biodegradable, and recyclable solid acid for the synthesis of quinoline derivatives via Friedländer annulation

Reddy, B. V. Subba; Venkateswarlu, A.; Reddy, G. Niranjan; Reddy, Y. V. R.

doi:10.1016/j.tetlet.2013.07.165

Cited by 50 publications

(13 citation statements)

References 58 publications

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“…Before 2015, significant resultsw ere achieved in 1) the synthesis of five-membered cyclic carbonatest hrough CO 2 /epoxide cycloadditions promoted by several chitosan-grafted ammoniums alts, including chitosan-supported ionic liquids; [53] 2) the synthesis of quinoline derivatives throughF riedländer annulation reactions catalyzed by chitosan-supported sulfonic acid; [54] and 3) the synthesis of heterocyclic compounds through Michael-type additions promoted by chitosan-grafted poly(4-vinylpyridine)c opolymers. [55] In addition, noteworthy results have been reported by Cui and co-workers in the context of stereoselective aldol and Henry reactions, [56] promoted by chitosan-immobilized l-proline, and asymmetric Michael additions, [57] promoted by chitosan-supported quinine and cinchonine.…”

Section: Chitosan-supported Organocatalystsmentioning

confidence: 99%

Valorization of Waste: Sustainable Organocatalysts from Renewable Resources

Meninno

2019

ChemSusChem

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443 Reviews Figure 2. Potential organocatalytic modes of activatione xhibited by chitosan.Scheme2.Monoglycerides ynthesis by ring opening of the glycidol catalyzed by chitosan. 444 ReviewsScheme3.Aldol reaction between 4-nitrobenzaldehyde (1)a nd cyclohexanone (2)promoted by chitosan hydrogel beads. Scheme4.Aldol reactionscatalyzed by dried chitosan gels and proposed catalytic modes of activation. 445 Reviews Scheme5.Aldol reaction in water promoted by chitosan aerogel beads (additivesu sed at 20 mol %: DNP = 2,4-dinitrophenol, SA = stearic acid, SDS = sodium dodecyl sulfate,B oc = tert-butyloxycarbonyl; ee = enantiomeric excess). Scheme6.Aldol reactionscatalyzedb yc hitosan in 1-butyl-3-methylimidazolium bromide ([bmim][Br])at3 78C. 446 Reviews Scheme16. Asymmetric aldol reaction in water catalyzedb yc hitosan-supported cinchonine. Scheme15. Chitosan-catalyzed transamidation of carboxamides with amines under neat conditions. 450 Reviews Scheme17. Knoevenagelcondensation of challenging aldehydes promoted by native and modified chitosan-derived hydrogels ([a] conversion valuesare reported). 458 Reviews Scheme33. Stereoselective Michael reaction catalyzedbyan aturalpinanederived bifunctional organocatalyst. Scheme32. Stereoselective Mannich reaction catalyzed by d-glucosamine-derived organocatalyst and the hypothetical reaction TS. 460 Reviews Scheme35. a) Synthesis of organocatalyst 52 derived from abietic acid. b) Asymmetric direct aldol reaction catalyzed by 52.c)Proposed TS model. 461 ReviewsScheme42. a) Reductive transformation of CO 2 with amines into formamidesand methylamines organocatalyzedbyl ecithin, and b) plausible reaction mechanism.

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Section: Chitosan-supported Organocatalystsmentioning

confidence: 99%

Valorization of Waste: Sustainable Organocatalysts from Renewable Resources

Meninno

2019

ChemSusChem

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“…e preparation method of chitosan sulfonic acid catalyst (CS-SO 3 H) with high acid density was modified with reference to the literature [23]. Specifically, 5.0 g chitosan powder was added into 50 mL dichloromethane and stirred to form a suspension.…”

Section: Preparation Of Catalystmentioning

confidence: 99%

Efficient Production of Methyl Oleate Using a Biomass-Based Solid Polymeric Catalyst with High Acid Density

Wang

Zhang

et al. 2019

Advances in Polymer Technology

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Biomass-based polymers are eco-friendly, nontoxic and biodegradable materials. In this work, in order to prepare green, low-cost and high-efficient catalysts under mild conditions, we chose biomass-based chitosan as raw material and prepared a new solid acidic catalyst by an acid functionalization method. FT-IR, XRD, SEM, TGA, BET, neutralization titration and other analytical methods were used to characterize the catalyst. The results showed that CS-SO3H morphology exhibited a sphere of about 10 μm diameter, and the acid density was as high as 3.81 mmol/g. The catalyst exhibits good catalytic activity in the esterification of oleic acid and methanol, which is a model reaction of the pre-esterification process in the preparation of biodiesel from feedstocks with high acid values. Under the optimum reaction conditions (15/1 methanol/oleic acid mole ratio and 3 wt% catalyst dosage at 75°C for 3 h), the yield of methyl oleate can reach 95.7%. Even if the mass of oleic acid in the reactant increased to 20 g, solid acid showed good catalytic performance, and the yield of methyl oleate was 94.4%. After four times of reuse, the yield of the catalyst can still reach 85.7%, which indicates that the catalyst has good catalytic activity and stability, and has potential application prospects.

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“…[41] The catalyst was prepared by treatment of a raw chitosan suspension with chlorosulfonic acid in pyridine. [41] The catalyst was prepared by treatment of a raw chitosan suspension with chlorosulfonic acid in pyridine.…”

Section: Brønsted Acid Catalysismentioning

confidence: 99%

Chitosan: An Upgraded Polysaccharide Waste for Organocatalysis

2015

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Green chemistry, directed towards the sustainable adaptation of human activity, is part of our society. Catalysis and waste upgrading are central aspects of green chemistry. Bringing them together would afford efficient chemical processes from the point of view of sustainability. Chitosan is a polyglucosamine generated from chitin, an abundant polysaccharide recycled from industrial marine wastes. Organocatalysts show some advantages over metallocatalysts in that they do not involve non‐renewable rare metals. However, they have drawbacks such as the need for high loadings and difficulties of recovery. This microreview presents recent achievements in the field of organocatalytic reactions promoted by chitosan as a heterogeneous catalytic material. Various organic reactions are reported, in which chitosan is engaged either as an insoluble organocatalyst or as a support for organocatalysts, being easily recycled and reused. Influences on the reaction outcomes are discussed. Although most reactions produce achiral products, a few asymmetric ones have emerged, demonstrating the capacity of chitosan to transfer its stereochemical information.

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Chitosan-SO3H: an efficient, biodegradable, and recyclable solid acid for the synthesis of quinoline derivatives via Friedländer annulation

Cited by 50 publications

References 58 publications

Valorization of Waste: Sustainable Organocatalysts from Renewable Resources

Valorization of Waste: Sustainable Organocatalysts from Renewable Resources

Efficient Production of Methyl Oleate Using a Biomass-Based Solid Polymeric Catalyst with High Acid Density

Chitosan: An Upgraded Polysaccharide Waste for Organocatalysis

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