Cyrene: a very reactive bio-based chiral ketone in diastereoselective Passerini reactions

Martinho, Luan A.; Rosalba, Thaíssa Pasquali F.; Sousa, Gustavo G; Gatto, Claudia C.; Politi, José R. S.; Andrade, Carlos Kleber Z.

doi:10.1007/s11030-023-10618-6

Cited by 3 publications

(2 citation statements)

References 36 publications

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“…Due to its already mentioned attractive intrinsic properties, HPW was used in our initial studies to find the best reaction conditions. Additionally, knowing that a higher temperature is crucial for faster GBB reactions, μw heating was used, taking into account our experience over the years on the μw-mediated MCRs [51][52][53]. 2-Aminopyridine (1a), 4-nitrobenzaldehyde (2a), and tert-butyl isocyanide (3a) were chosen as model substrates and different conditions were screened (Table 1).…”

Section: Resultsmentioning

confidence: 99%

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

Martinho,

Andrade

2024

Beilstein J. Org. Chem.

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The imidazo[1,2-a]pyridine moiety is present in drugs with several biological activities. The most direct way of obtaining this nucleus is the Groebke–Blackburn–Bienaymé three-component reaction (GBB-3CR) between aminopyridines, aldehydes, and isocyanides under both Lewis and Brønsted acid catalysis. However, several catalysts for this reaction have major drawbacks such as being expensive, extremely dangerous, strong oxidizing, and even explosive. In this scenario, heteropolyacids emerge as greener and safer alternatives due to their very strong Brønsted acidity. In particular, phosphotungstic acid (HPW) is an economical and green attractive catalyst for being cheap, non-toxic, and is known for its chemical and thermal stability. Herein, we report a straightforward approach to the GBB-3CR using HPW as catalyst in ethanol under microwave (μw) heating. This convenient environmentally benign methodology is broad in scope, provides the heterobicyclic products in high yields (up to 99%), with a low catalyst loading (2 mol %) in only 30 minutes, and allows the successful use of aliphatic aldehydes, substrates not so frequently explored with most usual catalysts for this reaction. Furthermore, the aforementioned advantages make this methodology very attractive and superior to the existing ones.

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Section: Resultsmentioning

confidence: 99%

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

Martinho,

Andrade

2024

Beilstein J. Org. Chem.

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“…De Bruyn et al have demonstrated that Cu and other metals supported on hydrotalcite can attain a high and stable catalytic activity for the hydrogenation of Cyrene, and this behaviour is independent of the exact pretreatment conditions [76]. Cyrene's chiral chemical structure displays excellent selectivity in Diels-Alder reactions, sulfa-Michael reactions or diastereoselective Passerini reactions [77][78][79][80]. Mencer and coworkers prepared a library of exo-cyclic carbohydrate enones 2-13 via a base-catalysed, highly stereoselective aldol condensation of Cyrene with various aromatic aldehydes [81].…”

Section: Cyrene For Extraction and Separationmentioning

confidence: 99%

Preparation and Application of Green Sustainable Solvent Cyrene

Wang,

Dai,

Luo

et al. 2023

Chemistry

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The bio-based solvent dihydrolevoglucosenone (Cyrene) is a green and sustainable alternative to petroleum-based dipolar aprotic solvents. Cyrene can be prepared from cellulose in a simple two-step process and can be produced in a variety of yields. Cyrene is compatible with a large number of reactions in the chemical industry and can be applied in organic chemistry, biocatalysis, materials chemistry, graphene and lignin processing, etc. It is also green, non-mutagenic and non-toxic, which makes it very promising for applications. In this paper, we have also screened all articles related to Cyrene on the Web of Science and visualised them through Cite Space.

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Renewable carbon resource from biomass: building molecular architectures from furanic platforms

López,

Porcal

2024

Pure and Applied Chemistry

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Currently, we find ourselves with the urgent need for chemistry to exert a substantial positive influence on environmental impact, by means of products and chemical processes. To achieve these objectives, we must pay special attention in terms of resource sustainability, considering factors such as life cycle assessments and minimizing carbon footprints. Biomass obtained from organic matter found in plants as well as agricultural and industrial waste, represents the most abundant reserve of renewable materials on our planet. In this perspective we highlight the research and innovation possibilities provided by renewable raw materials obtained from biomass within the domain of organic synthesis toward sustainable development. We focus our discussion on different reactions in the field of organic chemistry, primarily employing furanic platforms as renewable compounds derived from cellulosic biomass. The main aim is to generate high-value products, with a special emphasis on potential development of new pharmaceuticals.

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Cyrene: a very reactive bio-based chiral ketone in diastereoselective Passerini reactions

Cited by 3 publications

References 36 publications

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

Preparation and Application of Green Sustainable Solvent Cyrene

Renewable carbon resource from biomass: building molecular architectures from furanic platforms

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