scholarly journals Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1H-Isoindolin-1-Ones

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4527 ◽  
Author(s):  
Saira Mumtaz ◽  
Mark J. Robertson ◽  
Michael Oelgemöller
Keyword(s):  
Local Anesthetic ◽  
Continuous Flow ◽  
Reaction Times ◽  
Batch Processes ◽  
Thermal Flow

An effective multi-step continuous flow approach towards N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones, including the local anesthetic compound AL-12, has been realized. Compared to the traditional decoupled batch processes, the combined photochemical–thermal–thermal flow setup rapidly provides the desired target compounds in superior yields and significantly shorter reaction times.

Room Temperature Flow Electrochemistry as a Means of Retaining the “Memory of Chirality” via Hofer Moest Type Reaction

2020 ◽  
Author(s):  
Tomas Hardwick ◽  
Rossana Cicala ◽  
Nisar Ahmed
Keyword(s):  
Continuous Flow ◽  
Room Temperature ◽  
Biological Activities ◽  
Supporting Electrolyte ◽  
Enantiomeric Excess ◽  
Flow Chemistry ◽  
Batch Processes ◽  
Enabling Technology ◽  
Chiral Compounds ◽  
Memory Of Chirality

<p>Many chiral compounds have become of great interest to the pharmaceutical industry as they possess various biological activities. Concurrently, the concept of “memory of chirality” has been proven as a powerful tool in asymmetric synthesis, while flow chemistry has begun its rise as a new enabling technology to add to the ever increasing arsenal of techniques available to the modern day chemist. Here, we have employed a new simple electrochemical microreactor design to oxidise an L-proline derivative at room temperature in continuous flow. Flow performed in microreactors offers up a number of benefits allowing reactions to be performed in a more convenient and safer manner, and even allow electrochemical reactions to take place without a supporting electrolyte due to a very short interelectrode distance. By the comparison of electrochemical oxidations in batch and flow we have found that continuous flow is able to outperform its batch counterpart, producing a good yield (71%) and a better enantiomeric excess (64%) than batch with a 98% conversion. We have, therefore, provided evidence that continuous flow chemistry has the potential to act as a new enabling technology to replace some aspects of conventional batch processes. </p>

scholarly journals The Eschenmoser coupling reaction under continuous-flow conditions

2011 ◽  
Vol 7 ◽  
pp. 1164-1172 ◽  
Author(s):  
Sukhdeep Singh ◽  
J Michael Köhler ◽  
Andreas Schober ◽  
G Alexander Groß
Keyword(s):  
Continuous Flow ◽  
Elevated Temperatures ◽  
Reaction Times ◽  
Coupling Reaction ◽  
Flow Chemistry ◽  
Flow Conditions ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Reaction Proceeds

The Eschenmoser coupling is a useful carbon–carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated secondary thioamides or thiolactames, the Eschenmoser coupling needs prolonged reaction times and elevated temperatures to deliver valuable yields. We have used a flow chemistry system to promote the Eschenmoser coupling under enhanced reaction conditions in order to convert the demanding precursors such as S-alkylated secondary thioamides and thiolactames in an efficient way. Under pressurized reaction conditions at about 220 °C, the desired Eschenmoser coupling products were obtained within 70 s residence time. The reaction kinetics was investigated and 15 examples of different building block combinations are given.

scholarly journals Diels–Alder reactions of myrcene using intensified continuous-flow reactors

2017 ◽  
Vol 13 ◽  
pp. 120-126 ◽  
Author(s):  
Christian H Hornung ◽  
Miguel Á Álvarez-Diéguez ◽  
Thomas M Kohl ◽  
John Tsanaktsidis
Keyword(s):  
Continuous Flow ◽  
Flow Reactor ◽  
Scale Up ◽  
Reaction Times ◽  
Alder Reaction ◽  
Diels Alder ◽  
Flow Reactors ◽  
Diels Alder Reaction ◽  
Naturally Occurring ◽  
Continuous Flow Reactors

This work describes the Diels–Alder reaction of the naturally occurring substituted butadiene, myrcene, with a range of different naturally occurring and synthetic dienophiles. The synthesis of the Diels–Alder adduct from myrcene and acrylic acid, containing surfactant properties, was scaled-up in a plate-type continuous-flow reactor with a volume of 105 mL to a throughput of 2.79 kg of the final product per day. This continuous-flow approach provides a facile alternative scale-up route to conventional batch processing, and it helps to intensify the synthesis protocol by applying higher reaction temperatures and shorter reaction times.

Investigation on hemolytic effect of poly(lactic co-glycolic) acid nanoparticles synthesized using continuous flow and batch processes

nano Online ◽  
2018 ◽  
Author(s):  
Sumit Libi ◽  
Bogdan Calenic ◽  
Carlos E. Astete ◽  
Challa Kumar ◽  
Cristina M. Sabliov
Keyword(s):  
Continuous Flow ◽  
Glycolic Acid ◽  
Batch Processes ◽  
Hemolytic Effect

scholarly journals Continuous Flow Synthesis of Anticancer Drugs

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6992
Author(s):  
Mara Di Filippo ◽  
Marcus Baumann
Keyword(s):  
Anticancer Drugs ◽  
Continuous Flow ◽  
Flow Chemistry ◽  
Active Pharmaceutical Ingredient ◽  
Building Blocks ◽  
Short Review ◽  
Molecular Structures ◽  
Batch Processes ◽  
Continuous Flow Chemistry ◽  
The Impact

Continuous flow chemistry is by now an established and valued synthesis technology regularly exploited in academic and industrial laboratories to bring about the improved preparation of a variety of molecular structures. Benefits such as better heat and mass transfer, improved process control and safety, a small equipment footprint, as well as the ability to integrate in-line analysis and purification tools into telescoped sequences are often cited when comparing flow to analogous batch processes. In this short review, the latest developments regarding the exploitation of continuous flow protocols towards the synthesis of anticancer drugs are evaluated. Our efforts focus predominately on the period of 2016–2021 and highlight key case studies where either the final active pharmaceutical ingredient (API) or its building blocks were produced continuously. It is hoped that this manuscript will serve as a useful synopsis showcasing the impact of continuous flow chemistry towards the generation of important anticancer drugs.

scholarly journals Dimeric cyclobutane formation under continuous flow conditions using organophotoredox catalysed [2+2]-cycloaddition

2021 ◽  
Author(s):  
Helena Grantham ◽  
Marc Kimber
Keyword(s):  
Natural Products ◽  
Continuous Flow ◽  
Reaction Times ◽  
Functional Materials ◽  
Synthetic Route ◽  
Flow Conditions ◽  
Reaction Conditions ◽  
New Class ◽  
Cyclobutane Dimers ◽  
Flow Study

Radical cation-initiated dimerization of electron rich alkenes is an expedient method for the synthesis of cyclobutanes. By merging organophotoredox catalysis and continuous flow technology a batch versus continuous flow study has been performed providing a convenient synthetic route to an important carbazole cyclobutane material dimer t-DCzCB using less only 0.1 mol% of an organophotoredox catalyst. The scope of this methodology was explored giving a new class of functional materials, as well as an improved synthetic route to styrene based lignan dimeric natural products. The cyclobutane dimers could be isolated in higher chemical yields under continuous flow conditions and reaction times were reduced significantly compared to traditional batch reaction conditions.

scholarly journals Recent Advances in Continuous-Flow Reactions Using Metal-Free Homogeneous Catalysts

Catalysts ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 1321
Author(s):  
Naoto Sugisawa ◽  
Hiroyuki Nakamura ◽  
Shinichiro Fuse
Keyword(s):  
Continuous Flow ◽  
Low Cost ◽  
Reaction Times ◽  
Toxic Metal ◽  
Homogeneous Catalysts ◽  
Precise Control ◽  
Metal Free ◽  
Acidic Catalysts ◽  
Ready Availability ◽  
Low Toxicity

Developments that result in high-yielding, low-cost, safe, scalable, and less-wasteful processes are the most important goals in synthetic organic chemistry. Continuous-flow reactions have garnered much attention due to many advantages over conventional batch reactions that include precise control of short reaction times and temperatures, low risk in handling dangerous compounds, and ease in scaling up synthesis. Combinations of continuous-flow reactions with homogeneous, metal-free catalysts further enhances advantages that include low-cost and ready availability, low toxicity, higher stability in air and water, and increased synthetic efficiency due to the avoidance of the time-consuming removal of toxic metal traces. This review summarizes recently reported continuous-flow reactions using metal-free homogeneous catalysts and classifies them either as acidic catalysts, basic catalysts, or miscellaneous catalysts. In addition, we compare the results between continuous-flow conditions and conventional batch conditions to reveal the advantages of using flow reactions with metal-free homogeneous catalysts.

scholarly journals Microfluidic radiosynthesis of [18F]FEMPT, a high affinity PET radiotracer for imaging serotonin receptors

2017 ◽  
Vol 13 ◽  
pp. 2922-2927 ◽  
Author(s):  
Thomas Lee Collier ◽  
Steven H Liang ◽  
J John Mann ◽  
Neil Vasdev ◽  
J S Dileep Kumar
Keyword(s):  
Serotonin Receptors ◽  
Continuous Flow ◽  
Partial Agonist ◽  
Reaction Times ◽  
Radiochemical Yield ◽  
Reaction Parameters ◽  
High Affinity ◽  
Molar Activity ◽  
Chemical Purity ◽  
Radiochemical Yields

Continuous-flow microfluidics has shown increased applications in radiochemistry over the last decade, particularly for both pre-clinical and clinical production of fluorine-18 labeled radiotracers. The main advantages of microfluidics are the reduction in reaction times and consumption of reagents that often result in increased radiochemical yields and rapid optimization of reaction parameters for 18F-labeling. In this paper, we report on the two-step microfluidic radiosynthesis of the high affinity partial agonist of the serotonin 1A receptor, [18F]FEMPT (pK i = 9. 79; K i = 0.16 nM) by microfluidic radiochemistry. [18F]FEMPT was obtained in ≈7% isolated radiochemical yield and in >98% radiochemical and chemical purity. The molar activity of the final product was determined to be >148 GBq/µmol (>4 Ci/µmol).

scholarly journals Continuous flow synthesis of α-aryl-α-aminophosphonates

2019 ◽  
Vol 91 (1) ◽  
pp. 67-76 ◽  
Author(s):  
Erika Bálint ◽  
Ádám Tajti ◽  
Katalin Ladányi-Pára ◽  
Nóra Tóth ◽  
Béla Mátravölgyi ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Reaction Times ◽  
Primary Amines ◽  
Flow Process ◽  
Flow Synthesis ◽  
Microwave Reactor ◽  
Dialkyl Phosphites ◽  
Benzaldehyde Derivatives

AbstractThe synthesis of α-aryl-α-aminophosphonates was performed by the three-component Kabachnik-Fields reaction of primary amines, benzaldehyde derivatives and dialkyl phosphites in a continuous flow microwave reactor. The target compounds could be obtained in high (~90%) yields without any catalyst in simple alcohols as the solvent. The flow process elaborated required shorter reaction times and lower excess of the reagent, as compared to the “traditional” batch reactions, and allowed the synthesis of the α-aminophosphonates on a somewhat larger scale.

Protecting-group-free synthesis of hydroxyesters from amino alcohols

2020 ◽  
Vol 56 (74) ◽  
pp. 10938-10941
Author(s):  
Guillaume Reynard ◽  
Eve-Marline Joseph-Valcin ◽  
Hélène Lebel
Keyword(s):  
Carboxylic Acids ◽  
Continuous Flow ◽  
Amino Alcohols ◽  
Batch Processes ◽  
Protecting Group

The synthesis of hydroxyesters from carboxylic acids and unprotected amino alcohols in both continuous flow and batch processes is reported.

Sign in / Sign up

Export Citation Format

Share Document