First Examples of Doebner-Miller Reaction in Flow: Efficient Production of 2-Methylquinoline Derivatives in Water

Yalgin, Hasret; Luart, Denis; Len, Christophe

doi:10.1556/1846.2015.00044

Cited by 13 publications

(8 citation statements)

References 17 publications

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“…[1][2][3][4][5] However, the traditional liquidphase routes suffer from several limitations, such as, volatile organic solvents, expensive or toxic feedstocks and complicated recycling of catalysts. [6][7][8][9][10][11][12] Hence, the development of vaporphase synthesis is of great interest. Although many vaporphase syntheses of quinolines have been reported, most of them are not environment-friendly and uneconomical.…”

Section: Introductionmentioning

confidence: 99%

High-efficiency catalytic performance over mesoporous Ni/beta zeolite for the synthesis of quinoline from glycerol and aniline

et al. 2017

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Section: Introductionmentioning

confidence: 99%

High-efficiency catalytic performance over mesoporous Ni/beta zeolite for the synthesis of quinoline from glycerol and aniline

et al. 2017

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“…Various quinoline scaffolds with substituents at carbon-4 can be prepared through cascade reactions known as the Gould-Jacob cyclization reaction. 4 In this procedure 4-hydroxyquinoline 16 is prepared from aniline ( 14) and diethyl ethoxymethylenemalonate (15) involving series of reactions to provide quinoline 16 (Scheme 1).…”

Section: Gould-jacob Quinoline Synthesismentioning

confidence: 99%

“…Yalgin and co-workers report the synthesis of 2-methylquinoline 36 using a modied Doebner-von Miller reaction protocol in the presence of a strong acid in a ow reactor with aniline and acrolein. 15 procedure. This method is a rapid and green route for the synthesis of quinoline derivatives to provide a good to excellent yields (Scheme 7).…”

Section: Skraup/doebner-von Miller Quinoline Synthesismentioning

confidence: 99%

Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review

2020

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“…To achieve such a goal, using different anilines as starting materials and sulfuric acid as catalyst, the reaction was performed in a series of continuous stirred tank reactors (CSTRs), allowing higher yields and decreasing by‐product formation, when compared to the batch procedure (Scheme a) ) . In the same year, this reaction was also explored by Yalgin et al ., using an Omnifit column as the reactor and operating at higher temperature (Scheme b) ) . Both systems allowed similar yields.…”

Section: Heterocyclic Synthesismentioning

confidence: 99%

Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis

2019

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Flow Chemistry is a revolutionary field in Organic Chemistry. By changing the conventional methods and apparatus applied in the chemical synthesis, flow chemistry emerges as a game changer for organic synthesis laboratories, in both academia and industries. Considered as a sustainable practice, flow processes play an important role in the development of fine chemical products and in drug discovery development pro- [a] The main advantages of flow chemistry are that it allows the reaction to be carried out safely with high selectivity, high reproducibility and reduced energy consumption/carbon footprint. These features make this emerging technology for organic synthesis desirable for green and sustainable chemical synthesis, giving the chemist time for work planning and design, instead of using it in repetitive tasks, [5b,12] as expressed by the CHEM21 project by awarding a green flag for continuousflow reactions, in opposition to an amber flag for those performed under batch conditions. [13] Pedro Brandão received his MSc in Pharmaceutical Sciences from the Faculty of Pharmacy -University of Porto, in 2011. Pursuing his passion on studies in the field of Drug Discovery and Development, he is currently undergoing his PhD studies in Chemistry, in the field of Catalysis and Sustainability. His main focus of work is the discovery of new drug candidates through sustainable techniques. Marta Pineiro received her Ph.D. in Organic Chemistry in 2003 in the University of Coimbra, Portugal, and since 2002 has been enrolled at the University of Coimbra, being at present Auxiliary Professor. Her research interests are in the area of sustainable organic synthesis, microwave-assisted organic synthesis and synthesis and biological applications of tetrapyrrolic macrocycles. Teresa M. V. D. Pinho e Melo studied Chemistry at the University of Coimbra, where she graduated in 1985, got her M. 7191CPBA) as the oxidizing agent, avoiding the handling of this expensive and explosive reagent. [25] Recently, Morodo et al. explored the synthesis of two very important oxiranes (epichlorohydrin and glycidol) from biobased glycerol, under flow conditions. As depicted in Scheme 1, and using pimelic acid as the catalyst (10 mol-%), a sequential hydrochlorination/dichlorination process allows high conversion of glycerol (> 99 %) into 1,3-dichloro-2-propanol, followed by the quantitative conversion into a separable mixture of glycidol and epichlorohydrin (2:3). The separation of these two products is performed by an in-line membrane separation system, which allows the first product to be collected in the aqueous phase, while the second is collected in MTBE. This heterocycle can be further used as a synthetic precursor to relevant APIs bearing -amino alcohol moieties (e.g., propranolol, alprenolol and naftopidil). [26] Scheme 1. Sequential flow setup for the preparation of glycidol and epichlorohydrin, important APIs synthetic intermediates.Scheme 3. Synthesis and inline purification of a bicyclic aziridine (SGMR = silicon-glass microfluidic react...

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First Examples of Doebner-Miller Reaction in Flow: Efficient Production of 2-Methylquinoline Derivatives in Water

Cited by 13 publications

References 17 publications

High-efficiency catalytic performance over mesoporous Ni/beta zeolite for the synthesis of quinoline from glycerol and aniline

High-efficiency catalytic performance over mesoporous Ni/beta zeolite for the synthesis of quinoline from glycerol and aniline

Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review

Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis

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