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.

Continuous flow synthesis of amine oxides by oxidation of tertiary amines

2019 ◽  
Vol 4 (7) ◽  
pp. 1270-1276
Author(s):  
Tobias Baumeister ◽  
Stefan Zikeli ◽  
Hannes Kitzler ◽  
Paul Aigner ◽  
Piotr P. Wieczorek ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Continuous Flow ◽  
Tertiary Amines ◽  
Flow Process ◽  
Flow Synthesis ◽  
Amine Oxides ◽  
Continuous Flow Process

An efficient, safe and scalable continuous flow process for the synthesis of amine oxides with hydrogen peroxide is described.

scholarly journals The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

2017 ◽  
Vol 13 ◽  
pp. 76-86 ◽  
Author(s):  
Erika Bálint ◽  
Ádám Tajti ◽  
Anna Ádám ◽  
István Csontos ◽  
Konstantin Karaghiosoff ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Solvent Free ◽  
Primary Amines ◽  
Diphenylphosphine Oxide ◽  
Dimer Formation ◽  
X Ray ◽  
Microwave Assisted ◽  
Pudovik Reaction ◽  
Dialkyl Phosphites ◽  
Benzaldehyde Derivatives

A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N–H···O=P intermolecular hydrogen bridges pair.

scholarly journals Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3307
Author(s):  
Ádám Tajti ◽  
Nóra Tóth ◽  
Bettina Rávai ◽  
István Csontos ◽  
Pál Tamás Szabó ◽  
...  
Keyword(s):  
Reaction Time ◽  
Continuous Flow ◽  
Molar Ratio ◽  
Primary Amines ◽  
Diethyl Phosphite ◽  
The Novel ◽  
Dialkyl Phosphites ◽  
Ft Ir ◽  
High Yields ◽  
Real Time Information

A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, the reaction time and the molar ratio of the starting materials. To evaluate the potential of MW irradiation, comparative thermal experiments were also carried out. In order to obtain “real time” information about the condensation, the special Kabachnik–Fields reaction of 2-formylbenzoic acid, butylamine and diethyl phosphite was monitored by in situ FT-IR spectroscopy. The novel title compounds could be prepared in high yields at low temperature under a short reaction time. A suitable method could also be developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor.

Continuous-Flow Synthesis of (–)-Oseltamivir Phosphate (Tamiflu)

Synlett ◽  
2020 ◽  
Vol 31 (19) ◽  
pp. 1925-1929 ◽  
Author(s):  
Paul Watts ◽  
Cloudius R. Sagandira
Keyword(s):  
Residence Time ◽  
Continuous Flow ◽  
Shikimic Acid ◽  
Flow Process ◽  
Flow Synthesis ◽  
Continuous Flow Process ◽  
The Individual ◽  
Total Residence Time ◽  
Oseltamivir Phosphate

Herein the anti-influenza drug (–)-oseltamivir phosphate is prepared in continuous flow from ethyl shikimate with 54% overall yield over nine steps and total residence time of 3.5 min from the individual steps. Although the procedure involved intermediate isolation, the dangerous azide chemistry and intermediates involved were elegantly handled in situ. It is the first continuous-flow process for (–)-oseltamivir phosphate involving azide chemistry and (–)-shikimic acid as precursor.

A Two-Stage Continuous-Flow Synthesis of Spirooxazine Photochromic Dyes

2013 ◽  
Vol 66 (2) ◽  
pp. 172 ◽  
Author(s):  
Mark York ◽  
Adriana Edenharter
Keyword(s):  
Continuous Flow ◽  
Hydroxylamine Hydrochloride ◽  
Preliminary Evaluation ◽  
Substituted Anilines ◽  
Two Stage ◽  
Flow Process ◽  
Flow Synthesis ◽  
Continuous Flow Process

A continuous-flow process for the synthesis of several known and previously unreported spirooxazine photochromic dyes is reported. The process proceeds via an initial copper catalysed addition of substituted anilines to naphthalene-1,2-dione. This is followed by reaction with 1,3,3-trimethyl-2-methyleneindoline in the presence of hydroxylamine hydrochloride to give the desired spirooxazine products. The photochromic dyes were then cast into lenses to allow a preliminary evaluation of their properties.

scholarly journals Continuous Flow Synthesis of Propofol

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7183
Author(s):  
Romain Mougeot ◽  
Philippe Jubault ◽  
Julien Legros ◽  
Thomas Poisson
Keyword(s):  
Intensive Care ◽  
Intensive Care Medicine ◽  
Continuous Flow ◽  
Intravenous Anesthesia ◽  
Flow Process ◽  
Short Acting ◽  
Flow Synthesis ◽  
Step Procedure ◽  
Continuous Flow Process

Herein, we report a continuous flow process for the synthesis of 2,6-diisopropylphenol—also known as Propofol—a short-acting intravenous anesthesia, widely used in intensive care medicine to provide sedation and hypnosis. The synthesis is based on a two-step procedure: a double Friedel–Crafts alkylation followed by a decarboxylation step, both under continuous flow.

Opportunities and Challenges for Nanoparticle Synthesis using Continuous Flow Systems: A Magnetite Nanocluster Case Study

2019 ◽  
Author(s):  
Erika Fong ◽  
Jinkyu Han ◽  
C. Cameron Cornell ◽  
Yong Han
Keyword(s):  
Continuous Flow ◽  
Solvothermal Synthesis ◽  
Elevated Temperatures ◽  
Nanoparticle Synthesis ◽  
Reaction Times ◽  
Reaction Chamber ◽  
Flow Speed ◽  
Magnetite Nanoparticle ◽  
Flow Synthesis ◽  
Nanoparticle Clusters

<div>In this study, we demonstrate a new high temperature flow synthesis system for magnetite nanoparticle clusters. We find that successful synthesis of nanoparticle clusters is dependent on residence time in the reaction chamber and linear flow speed. The long reaction times and elevated temperatures required, combined with the resulting slurry formed with successful magnetite nanocluster synthesis, made this reaction challenging to adapt to a flow system. However, proper design of a continuous flow synthesis platform and synthesis parameter control allows for the adoption of even difficult solvothermal synthesis processes. We discuss the importance of reaction pressure control and reaction duration for successful synthesis of magnetite nanoclusters and address opportunities and challenges associated with adopting solvothermal synthesis to continuous flow synthesis platforms.</div>

scholarly journals Continuous-flow synthesis of dimethyl fumarate: a powerful small molecule for the treatment of psoriasis and multiple sclerosis

RSC Advances ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 2490-2494 ◽  
Author(s):  
Marcelo T. Lima ◽  
Fernanda G. Finelli ◽  
Alline V. B. de Oliveira ◽  
Vinicius Kartnaller ◽  
João F. Cajaiba ◽  
...  
Keyword(s):  
Multiple Sclerosis ◽  
Small Molecule ◽  
Continuous Flow ◽  
Reaction Times ◽  
Pharmaceutical Preparations ◽  
Dimethyl Fumarate ◽  
Flow Synthesis

Dimethyl fumarate (DMF) has recently gained attention due to its use as a pro-drug in different pharmaceutical preparations, here in we present our work on a cascade methodology in short reaction times and quantitative yields.

scholarly journals Metal-porphyrin catalyzed aziridination of α-methylstyrene: Batch vs. flow process

2017 ◽  
Vol 21 (04-06) ◽  
pp. 381-390 ◽  
Author(s):  
Daniela Intrieri ◽  
Sergio Rossi ◽  
Alessandra Puglisi ◽  
Emma Gallo
Keyword(s):  
Dft Calculations ◽  
Continuous Flow ◽  
Flow System ◽  
Reaction Times ◽  
Batch Process ◽  
Porphyrin Ring ◽  
Flow Conditions ◽  
Metal Porphyrin ◽  
Flow Process ◽  
Influence Of Substituents

This work describes the aziridination process of [Formula: see text]-methylstyrene by using electron poor aromatic azides in the presence of metal-based porphyrins as catalysts. Different ruthenium and cobalt-based porphyrins were successfully employed for the synthesis of [Formula: see text]-aryl aziridines performed under a traditional batch methodology and under continuous flow conditions. In general, yields obtained using ruthenium-based catalysts in a traditional batch process were higher than those observed when the reaction was performed under flow conditions. However, cobalt-based porphyrins showed better activities and short reaction times when employed in a flow system process. DFT calculations were also performed in order to understand the influence of substituents on the porphyrin ring in the aziridination process.

Opportunities and Challenges for Nanoparticle Synthesis using Continuous Flow Systems: A Magnetite Nanocluster Case Study

2019 ◽  
Author(s):  
Erika Fong ◽  
Jinkyu Han ◽  
C. Cameron Cornell ◽  
Yong Han
Keyword(s):  
Continuous Flow ◽  
Solvothermal Synthesis ◽  
Elevated Temperatures ◽  
Nanoparticle Synthesis ◽  
Reaction Times ◽  
Reaction Chamber ◽  
Flow Speed ◽  
Magnetite Nanoparticle ◽  
Flow Synthesis ◽  
Nanoparticle Clusters

<div>In this study, we demonstrate a new high temperature flow synthesis system for magnetite nanoparticle clusters. We find that successful synthesis of nanoparticle clusters is dependent on residence time in the reaction chamber and linear flow speed. The long reaction times and elevated temperatures required, combined with the resulting slurry formed with successful magnetite nanocluster synthesis, made this reaction challenging to adapt to a flow system. However, proper design of a continuous flow synthesis platform and synthesis parameter control allows for the adoption of even difficult solvothermal synthesis processes. We discuss the importance of reaction pressure control and reaction duration for successful synthesis of magnetite nanoclusters and address opportunities and challenges associated with adopting solvothermal synthesis to continuous flow synthesis platforms.</div>

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