Continuous‐flow syntheses of heterocycles

Glasnov, Toma N.; Kappe, C. Oliver

doi:10.1002/jhet.568

Cited by 58 publications

(17 citation statements)

References 86 publications

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“…During the last decade there has been a steady growth in interest within the chemical community for flow based approaches to synthetic targets due to the inherent benefits such as automated and telescoped reaction sequences, quick reaction optimizations and in‐line work‐up and purification . The holistic nature of flow chemistry targets many aspects of both synthesis methodology and process engineering deriving both environmental and economic drivers.…”

Section: An Alternative Synthesis Strategymentioning

confidence: 99%

The integration of flow reactors into synthetic organic chemistry

Baxendale

2013

J of Chemical Tech & Biotech

244

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The material presented in this review is based upon discussions and interactions with members of the Department of Chemistry and Biochemistry within the University of Windsor, Ontario, Canada. This article explores the changing face of chemical synthesis with regard to the impact of flow based chemical processing technologies. Highlighted works from the Innovative Technology Centre (ITC), Cambridge, UK, are used to illustrate the alternative synthetic practices available to modern research chemists. The dominant theme of the review is the synergistic effects encountered by combining the advantages of continuous processing regimes with the power of immobilized reagents and scavenger systems for multi‐step organic chemistry. © 2012 Society of Chemical Industry

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Section: An Alternative Synthesis Strategymentioning

confidence: 99%

The integration of flow reactors into synthetic organic chemistry

Baxendale

2013

J of Chemical Tech & Biotech

244

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“…Among the variety of small-scale continuous-flow apparatus, micro-flow systems (‘microreactors’) [ 15 ] are the spearhead of process intensification innovation, and the chemical process technique called ‘flow chemistry’ [ 16 , 17 , 18 , 19 ] aimed at pharmaceutical synthesis is their major application. A simple and even inherent advantage of these micro-flow systems is related to their small inner volumes, which also means small volumes of processed chemicals used during experimental synthesis [ 17 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Micro Droplet Formation towards Continuous Nanoparticles Synthesis

et al. 2018

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In this paper, micro droplets are generated in a microfluidic focusing contactor and then they move sequentially in a free-flowing mode (no wall contact). For this purpose, two different micro-flow glass devices (hydrophobic and hydrophilic) were used. During the study, the influence of the flow rate of the water phase and the oil phase on the droplet size and size distribution was investigated. Moreover, the influence of the oil phase viscosity on the droplet size was analyzed. It was found that the size and size distribution of the droplets can be controlled simply by the aqueous phase flow rate. Additionally, 2D simulations to determine the droplet size were performed and compared with the experiment.

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“…69 A promising continuous flow condition for the Biginelli reaction has already been described by Kappe and coworkers. 70 This landmark publication 70 highlighted the potential of the strategy for the Biginelli MCR, and a later review by Kappe and Glasnov,71 pointed to the importance of new and efficient catalysts for this transformation under continuous flow conditions and for other heterocyclic syntheses. In this context, we have started optimizing the model reaction for a continuous flow protocol using CP 1 as the heterogeneous catalyst.…”

Section: Resultsmentioning

confidence: 99%

The Biginelli reaction under batch and continuous flow conditions: catalysis, mechanism and antitumoral activity

et al. 2015

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Two novel coordination polymers (CPs) have been synthesized, characterized and successfully applied as robust heterogeneous catalysts for the Biginelli multicomponent reaction to obtain 3,4dihydropyrimidin-2(1H)-one or thione (DHPMs) derivatives. The reaction was initially developed using both CPs and the Zn-based material showed much better catalytic activity. After the reaction optimization under batch conditions, a continuous flow protocol was developed and applied with impressive results. Four bioactive DHPMs were successfully synthesized with high yields. The mechanism of the transformation was also investigated by electrospray (tandem) mass spectrometry (ESI-MS(/MS)) analyses. Online monitoring of the reaction indicated under the developed conditions that the iminium mechanism is preferred over the enamine-and Knoevenagel-based mechanisms. Nine DHPMs had their antitumoral activities evaluated against MCF-7 (human breast cancer cells), A549 (human alveolar basal epithelial cells) and Caco-2 (human epithelial colorectal cells) cancer cell lineages. Fibroblasts (healthy cells) were not affected by the tested DHPMs showing an excellent selectivity for tumour cells. Three DHPMs returned impressive results, being capable of inhibiting tumour cell proliferation in 72 h.

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Continuous‐flow syntheses of heterocycles

Abstract: This review surveys the synthesis of heterocycles under continuous‐flow conditions, including the use of chip‐based microreactors, coil‐based flow reactors, and capillary or tubular devices. J. Heterocyclic Chem., 2011.

Cited by 58 publications

References 86 publications

The integration of flow reactors into synthetic organic chemistry

The integration of flow reactors into synthetic organic chemistry

Micro Droplet Formation towards Continuous Nanoparticles Synthesis

The Biginelli reaction under batch and continuous flow conditions: catalysis, mechanism and antitumoral activity

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