Reductive amination with a scavenger: The most “combinatorial” of two-component reactions

Ivanova, N.V.; Tkach, Natalia; Belykh, Eugene N.; Dlinnykh, I. V.; Бабаев, Е. В.

doi:10.1134/s1070363210120285

Cited by 4 publications

(6 citation statements)

References 12 publications

(14 reference statements)

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“…The stoichiometric reagents and the catalysts participate directly as part of the reaction itself, while the scavenger resins are typically applied after the reaction has occurred . Each of these classes, through the help of combinatorial chemistry, have been used in the synthesis of numerous compounds . Scavenging resins are mainly used for the removal of impurities and/or excess reagent in the reaction medium; this has been demonstrated as one of the major advantages of this technique in that the product of the reaction is not impaired since the residuals can be removed from the aqueous or organic solution .…”

Section: Introductionmentioning

confidence: 99%

Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Oliveira

Kartnaller

Pedrosa

et al. 2015

J of Applied Polymer Sci

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Over the past years, polymer-supported reagents have been extensively studied and used in various applications. One class of such reagents is called "scavengers," which can be used to easily eliminate compounds in a solution. The present work describes the production of a resin that can be used for scavenging ketones and aldehydes using low-cost reagents and simple reaction steps, named here Amb15-Iso. This resin is obtained by reacting a low-cost commercial sulfonyl resin, Amberlyst-15, with isoniazid, a drug used for the treatment of tuberculosis. Acetone and isobutyraldehyde were used as carbonyl compound models. The reactions were monitored in-line by ATR-FTIR and results showed that the polarity of the solvent influences the kinetics of the production of the resin and water proved to be the fastest solvent. For the scavenging of acetone and isobutyraldehyde, two factors showed to have an impact in the amount of compounds captured: the polarity of the solvent and the solubility of water in the solvent. The capacity of scavenging acetone in water varied from 0.11 to 0.28 mmol per gram of resin, depending on the initial acetone concentration. The equilibrium of this reaction was modeled and the equilibrium constant was calculated to be 0.63 6 0.07 L mol 21 . The resin was also recycled and tested in a second round of scavenging and results showed that there was not much difference between the new resin and the recycled one, proving that the Amberlyst-15 could be reused for a second cycle of scavenging. V C 2015 Wiley Periodicals, Inc. J.Appl. Polym. Sci. 2015, 132, 42291.

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Section: Introductionmentioning

confidence: 99%

Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Oliveira

Kartnaller

Pedrosa

et al. 2015

J of Applied Polymer Sci

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“…9h) the very bottom, a gas pressure is applied, due to which the solvent is forced through a system of prelabeled tubings into 24 receivers. We used just this technique in our training task [4].…”

Section: Parallel Filtrationmentioning

confidence: 99%

“…If some reaction components (for example, amine, base, or acid) were taken in excess and are present in the final reaction mixture, they are reliably removed by scavengers. Technical details of operation with a simple scavenger are discussed in [4].…”

Section: Parallel Purificationmentioning

confidence: 99%

Little artifices of huge libraries: Secrets of parallel liquid-phase synthesis

Бабаев

2010

Russ J Gen Chem

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Abstract-Key aspects of differences between liquid-phase parallel synthesis and preparation of a single compound at a time are reviewed. Specific technique and equipment is required to make in the parallel manner such processes as heating (involving MW ovens and flow microreactors), extraction, filtration, and chromatography. Rich illustrations may be useful in educational courses on medicinal and combinatorial chemistry.

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“…Unlike the reductive аmination task [3], where on filtering on Syncore we collected mother liquors, in the given task we collect and separate precipitates remaining in the reaction vessels. On filtering (Fig.…”

Section: Lesson 2 Product Isolationmentioning

confidence: 99%

“…The Moscow group first experimented with training tasks on solid-phase synthesis [1,2], and the task in parallel liquid-phase synthesis involved reductive amination [3]. After the MSU had acquired instrumentation for parallel filtration, a necessity arose to find an illustrative training task.…”

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confidence: 99%

A parallel Ugi reaction at students laboratories in the Ural and Moscow

Mironov¹,

Бабаев

2010

Russ J Gen Chem

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Abstract-A four-component Ugi reaction was adapted for students education. To this end, a series of almost odorless aromatic isonitriles with donor substituents was reacted with a specific carboxylic acid, phthaloyl glycine, to obtain poorly soluble (although nicely crystallized) products. The process was performed and compared in two versions by using (1) a standard centrifuge for parallel separation of precipitates and (2) parallel filtration with SynCore apparatus. It is shown for a broad series of aliphatic ketones and benzyl amines that the yields are satisfactory and the products require no further purification.In 2000-2001, at the Ural State Technical University, Yekaterinburg, there was developed a "Combinatorial Chemistry" laboratory training course for third year students specializing in biotechnology. The aim of this laboratory course was to develop practical skills in the field of parallel synthesis and consolidate the lecture material on combinatorial chemistry. Taking into account the basic student' training level, we had to find a simple and illustrative example of the parallel organic synthesis technology. The Ugi reaction is an ideal decision, since it allows compound libraries to be obtained without a complex equipment and hardly accessible reagents. The reagents were chosen so that to obtain precipitates which could be separated in parallel by centrifuging. It should be mentioned that the Ugi reaction is also used at students laboratories at some foreign universities (for example, at the Munich Technical University).The practical work at the USTU was envisioned for four lessons: an introductory workshop and three practical lessons. For fourth year students, an extended program comprising five practical lessons requiring a higher level basic training was suggested. In the first part of this paper we present a series of procedures and instructions which can help one to include the Ugi reaction in any laboratory training in combinatorial chemistry.Almost simultaneously, special laboratory training in combinatorial chemistry for fifth year students was initiated at the Lomonosov MSU. The Moscow group first experimented with training tasks on solid-phase synthesis [1,2], and the task in parallel liquid-phase synthesis involved reductive amination [3]. After the MSU had acquired instrumentation for parallel filtration, a necessity arose to find an illustrative training task. After the heads of these training courses (the authors of the present paper) had met face-to-face and exchanged experience, the Moscow group attempted to adapt the procedure developed at the USTU for use for the Syncore reactor (I. Dlinnykh, E. Belykh, and V. Alifanov were involved in this work in different times). In the second part of this paper we present the results of this experiment. In our opinion, the experience in such collaboration may be of interest for other universities. Basic Information on the Ugi ReactionWe consider it useful, to start with a workshop on the methodology of parallel synthesis and application of mu...

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Reductive amination with a scavenger: The most “combinatorial” of two-component reactions

Cited by 4 publications

References 12 publications

Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Little artifices of huge libraries: Secrets of parallel liquid-phase synthesis

A parallel Ugi reaction at students laboratories in the Ural and Moscow

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