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The Influence of Phase Transfer Catalysis (PTC) in the Synthesis...
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The Influence of Phase Transfer Catalysis (PTC) in the Synthesis of Bioactive Compounds

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (31 October 2022) | Viewed by 11527

Special Issue Editors

Dr. Jolanta Jaśkowska

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Guest Editor
Institute of Organic Chemistry and Technology, Faculty of Chemical and Engineering and Technology, Cracow University of Technology, 24 Warszawska Street, 31-155 Cracow, Poland
Interests: bioactive compounds; solvent-free synthesis; mechanochemistry; sonochemistry; synthesis in the presence of microwave radiation; phase transfer catalysis (PTC); green chemistry; serotonin receptor ligands; dopamine receptor ligands; API (active pharmaceutical ingredient)
Dr. Edyta Pindelska

E-Mail Website
Guest Editor
Department of Analytical Chemistry and Biomaterials, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-093 Warsaw, Poland
Interests: molecular crystal engineering; solid state chemistry; hydrogen bonding; crystal polymorphism; solid networks; solid-state API (active pharmaceutical ingredient); molecular and ionic co-crystals; solvent-free reactions; DFT calculations
Dr. Przemysław Jodłowski

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Guest Editor
Institute of Organic Chemistry and Technology, Faculty of Chemical and Engineering and Technology, Cracow University of Technology, 24 Warszawska Street, 31-155 Cracow, Poland
Interests: heterogeneous catalysis; sonochemistry; spectroscopy; structured reactors; metal–organic frameworks; zeolites; metal oxide catalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In recent years, research efforts have focused on the search for methods of synthesis of bioactive compounds that are characterized by a simplicity of the individual stages of the process and the use of readily available and safe reagents while maintaining high selectivity and efficiency. Moreover, especially in larger-scale reactions, the aspect of limiting the amount of harmful and environmentally toxic byproducts and waste is important. All these conditions are met by phase transfer catalysis (PTC). A wide variety of reactions can be carried out under PTC conditions, such as alkylation, oxidation, reduction, elimination, hydrolysis, aliphatic and aromatic substitution, multiple bond addition, carbonyl addition, and many others. Additionally, it is possible to use PTC conditions both in classical methods of synthesis and in the presence of microwave radiation, ultrasounds or in mechanochemistry. The obtained products, often even unpurified, are characterized by high purity, which is extremely important in the case of bioactive compounds. All these advantages of the PTC method mean that it is now used more and more often in the synthesis of bioactive compounds.

This Special Issue aims to cover the most recent progress and advances in the field of synthesis of bioactive compounds under phase transfer catalysis conditions. This includes both reactions using the PTC method in one or more steps, aimed at the synthesis of new bioactive compounds, and processes aimed at the development of new alternative methods of known drugs.

Dr. Jolanta Jaśkowska
Dr. Edyta Pindelska
Dr. Przemysław Jodłowski
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Catalysts is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • phase transfer catalysis (PTC)
  • bioactive compounds
  • solvent-free synthesis
  • mechanochemistry
  • sonochemistry
  • synthesis in the presence of microwave radiation

Published Papers (6 papers)

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Research

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14 pages, 2572 KiB  
Article
Phase-Transfer Catalyzed Microfluidic Glycosylation: A Small Change in Concentration Results in a Dramatic Increase in Stereoselectivity
by Ilya V. Myachin and Leonid O. Kononov
Catalysts 2023, 13(2), 313; https://0-doi-org.brum.beds.ac.uk/10.3390/catal13020313 - 01 Feb 2023
Cited by 4 | Viewed by 1528
Abstract
Phase-transfer catalysis (PTC) is widely used in glycochemistry for the preparation of aryl glycosides by the glycosylation reaction. While investigating the possibility of synthesis of 4-(3-chloropropoxy)phenyl sialoside (Neu5Ac-OCPP) from N-acetylsialyl chloride with O-acetyl groups (1), we have recently discovered [...] Read more.
Phase-transfer catalysis (PTC) is widely used in glycochemistry for the preparation of aryl glycosides by the glycosylation reaction. While investigating the possibility of synthesis of 4-(3-chloropropoxy)phenyl sialoside (Neu5Ac-OCPP) from N-acetylsialyl chloride with O-acetyl groups (1), we have recently discovered a strong dependence of the PTC glycosylation outcome on the mixing mode: under batch conditions, only α-anomer of Neu5Ac-OCPP was obtained, albeit in low yield (13%), while under microfluidic conditions the yield of Neu5Ac-OCPP increased to 36%, although stereoselectivity decreased (α/β ≤ 6.2). Here, we report that the outcome of this reaction, performed under microfluidic conditions using a Comet X-01 micromixer (at 2 μL/min flow rate), non-linearly depends on the concentration of N-acetylsialyl chloride 1 (5–200 mmol/L). The target Neu5Ac-OCPP was obtained in a noticeably higher yield (up to 66%) accompanied by enhanced stereoselectivity (α/β = 17:1–32:1) in the high concentration range (C > 50 mmol/L), whereas the yield (10–36%) and especially, stereoselectivity (α/β = 0.9:1–6.2:1) were lower in the low concentration range (C ≤ 50 mmol/L). This dramatic stepwise increase in stereoselectivity above critical concentration (50 mmol/L) is apparently related to the changes in the presentation of molecules on the surface of supramers of glycosyl donor, which exist in different concentration ranges. Full article
(This article belongs to the Special Issue The Influence of Phase Transfer Catalysis (PTC) in the Synthesis of Bioactive Compounds)
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11 pages, 2850 KiB  
Article
Synthesis of 3,4-Dihydropyridin-2-ones via Domino Reaction under Phase Transfer Catalysis Conditions
by Domenico C. M. Albanese, Nicoletta Gaggero and Kamila Prenga
Catalysts 2023, 13(1), 170; https://0-doi-org.brum.beds.ac.uk/10.3390/catal13010170 - 11 Jan 2023
Viewed by 1327
Abstract
3,4-dihydropyridin-2-ones are of considerable importance due to the large number of these core structures exhibiting a diverse array of biological and pharmacological activities. The Michael-type addition of 1,3-dithiane-2-carbothioates to α,β-unsaturated N-tosyl imines, followed by intramolecular annulation driven by a [...] Read more.
3,4-dihydropyridin-2-ones are of considerable importance due to the large number of these core structures exhibiting a diverse array of biological and pharmacological activities. The Michael-type addition of 1,3-dithiane-2-carbothioates to α,β-unsaturated N-tosyl imines, followed by intramolecular annulation driven by a sulfur leaving group, provides a practical reaction cascade for the synthesis of a variety of substituted 3,4-dihydropyridin-2-ones. In this work, the reaction was carried out under solid–liquid phase transfer catalysis (SL-PTC) conditions at room temperature, in short reaction times in the presence of cheap Bu4N+HSO4– and solid KOH. The new PTC method exhibited adequate functional group tolerance, proving to be a green and reliable method and easy to scale up to furnish rapid access to 3,4-dihydropyridin-2-ones after desulfurization from simple, readily available starting materials. Full article
(This article belongs to the Special Issue The Influence of Phase Transfer Catalysis (PTC) in the Synthesis of Bioactive Compounds)
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14 pages, 1448 KiB  
Article
Regio- and Stereoselective One-Pot Synthesis of New Heterocyclic Compounds with Two Selenium Atoms Based on 2-Bromomethyl-1,3-thiaselenole Using Phase Transfer Catalysis
by Svetlana V. Amosova, Andrey S. Filippov, Vladimir A. Potapov and Alexander I. Albanov
Catalysts 2022, 12(10), 1236; https://0-doi-org.brum.beds.ac.uk/10.3390/catal12101236 - 14 Oct 2022
Cited by 1 | Viewed by 1307
Abstract
To date, not a single representative of 2,3-dihydro-1,4-thiaselenin-2-yl selenides has been described in the literature. The reaction of 2-bromomethyl-1,3-thiaselenole with potassium selenocyanate at low temperature was accompanied by a rearrangement with ring expansion leading to six-membered 2,3-dihydro-1,4-thiaselenin-2-yl selenocyanate, which was used for the [...] Read more.
To date, not a single representative of 2,3-dihydro-1,4-thiaselenin-2-yl selenides has been described in the literature. The reaction of 2-bromomethyl-1,3-thiaselenole with potassium selenocyanate at low temperature was accompanied by a rearrangement with ring expansion leading to six-membered 2,3-dihydro-1,4-thiaselenin-2-yl selenocyanate, which was used for the generation of sodium dihydro-1,4-thiaselenin-2-yl selenolate. The latter intermediate was involved in situ in the nucleophilic substitution and addition reactions under phase transfer catalysis conditions. The nucleophilic substitution reactions with alkyl halides gave alkyl, allyl and propargyl 2,3-dihydro-1,4-thiaselenin-2-yl selenides in 93–98% yields. The addition reactions of dihydro-1,4-thiaselenin-2-yl selenolate anion to alkyl acrylates, acrylonitrile and alkyl propiolates proceeded in a regio- and stereoselective fashion affording corresponding functionalized 2,3-dihydro-1,4-thiaselenin-2-yl selenides in 93–98% yields. Thus, the regio- and stereoselective one-pot synthesis of a novel family of 2,3-dihydro-1,4-thiaselenin-2-yl selenides has been developed based 2-bromomethyl-1,3-thiaselenole, potassium selenocyanate, alkyl halides and compound with activated double and triple bonds. Full article
(This article belongs to the Special Issue The Influence of Phase Transfer Catalysis (PTC) in the Synthesis of Bioactive Compounds)
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15 pages, 2730 KiB  
Article
Regioselective Synthesis of Novel Functionalized Dihydro-1,4-thiaselenin-2-ylsufanyl Derivatives under Phase Transfer Catalysis
by Andrey S. Filippov, Svetlana V. Amosova, Alexander I. Albanov and Vladimir A. Potapov
Catalysts 2022, 12(8), 889; https://0-doi-org.brum.beds.ac.uk/10.3390/catal12080889 - 12 Aug 2022
Cited by 2 | Viewed by 1045
Abstract
The regioselective one-pot synthesis of novel functionalized 2,3-dihydro-1,4-thiaselenin-2-ylsufanyl derivatives in high yields based on 2-bromomethyl-1,3-thiaselenole and activated alkenes was developed under phase transfer catalysis conditions. The reactions proceed under mild conditions at room temperature in a regioselective manner with the addition of sodium [...] Read more.
The regioselective one-pot synthesis of novel functionalized 2,3-dihydro-1,4-thiaselenin-2-ylsufanyl derivatives in high yields based on 2-bromomethyl-1,3-thiaselenole and activated alkenes was developed under phase transfer catalysis conditions. The reactions proceed under mild conditions at room temperature in a regioselective manner with the addition of sodium dihydro-1,4-thiaselenin-2-ylthiolate exclusively at the terminal carbon atom of the double bond of vinyl methyl ketone, alkylacrylates, acrylamide, acrylonitrile, divinyl sulfone, and divinyl sulfoxide. The sodium dihydro-1,4-thiaselenin-2-ylthiolate was generated from 2-[amino(imino)methyl]sulfanyl-2,3-dihydro-1,4-thiaselenine hydrobromide. The latter compound was obtained by the reaction of 2-bromomethyl-1,3-thiaselenole with thiourea, which was accompanied by a rearrangement with ring expansion to the six-membered heterocycle. The obtained 2,3-dihydro-1,4-thiaselenin-2-ylsufanyl derivatives are a novel family of compounds with putative biological activity. The addition products of sodium dihydro-1,4-thiaselenin-2-ylthiolate at one double bond of divinyl sulfone and divinyl sulfoxide, containing vinylsulfonyl and vinylsulfinyl groups, are capable of further addition reactions. A possibility to obtain corresponding alcohol derivatives was shown in the reaction with vinyl methyl ketone. Full article
(This article belongs to the Special Issue The Influence of Phase Transfer Catalysis (PTC) in the Synthesis of Bioactive Compounds)
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15 pages, 1288 KiB  
Article
Mechanochemical Synthesis Method for Drugs Used in the Treatment of CNS Diseases under PTC Conditions
by Jolanta Jaśkowska, Anna Karolina Drabczyk, Piotr Michorczyk, Damian Kułaga, Przemysław Zaręba, Przemysław Jodłowski, Zbigniew Majka, Jarosław Jakubski and Edyta Pindelska
Catalysts 2022, 12(5), 464; https://0-doi-org.brum.beds.ac.uk/10.3390/catal12050464 - 21 Apr 2022
Cited by 5 | Viewed by 2060
Abstract
Phase transfer catalysis (PTC) is an excellent possibility in the synthesis of organic compounds as it allows the reactions to be carried out under the conditions of green chemistry, while maintaining high yields and selectivity. The great advantage of these reactions is also [...] Read more.
Phase transfer catalysis (PTC) is an excellent possibility in the synthesis of organic compounds as it allows the reactions to be carried out under the conditions of green chemistry, while maintaining high yields and selectivity. The great advantage of these reactions is also the possibility of carrying out the reactions not only under conventional conditions, but also mechanochemically in solvent-free processes. Bearing this in mind, we decided to develop a new method for the synthesis of known biologically active compounds from the group of long-chain arylpiperazines (LCAPs). The first mortar trials were very promising and prompted us to carry out a series of ball mill reactions. One of the technological problems that we encountered while conducting reactions in the ball mill was the difficulty in extracting the post-reaction mixture. We tested the effects of additives improving the insulation of the product, such as, e.g., starch, zeolites, and silica. Research has proven that with appropriate process conditions using TBAB as a catalyst and in the presence of potassium carbonate and a small amount of Zeolite ZSM5 or silica, aripiprazole can be obtained with a yield of 90% in just five minutes. The obtained results are very promising and it is worth considering them as an alternative to the synthesis of other compounds from the LCAPS group. Full article
(This article belongs to the Special Issue The Influence of Phase Transfer Catalysis (PTC) in the Synthesis of Bioactive Compounds)
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Review

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41 pages, 10006 KiB  
Review
Ionic Liquids: Advances and Applications in Phase Transfer Catalysis
by Stavros P. Neofotistos, Andromachi Tzani and Anastasia Detsi
Catalysts 2023, 13(3), 474; https://0-doi-org.brum.beds.ac.uk/10.3390/catal13030474 - 25 Feb 2023
Cited by 7 | Viewed by 2755
Abstract
Ionic liquids are a family of liquids that are composed entirely of ions and usually have melting points lower than 100 °C. Extensive research, along with the ever-growing interest of the scientific community, allowed for the development of a multitude of ionic liquids [...] Read more.
Ionic liquids are a family of liquids that are composed entirely of ions and usually have melting points lower than 100 °C. Extensive research, along with the ever-growing interest of the scientific community, allowed for the development of a multitude of ionic liquids with low melting points. Such compounds are considered neoteric materials as well as ideal, custom-made solvents for a variety of different chemical transformations. In this regard, the importance of phase transfer catalysis is evident in a diversity of substrates and reactions. The use of phase transfer catalysts allows the reaction to proceed, facilitating the transfer of otherwise insoluble reactants to the desired phase. Recent scientific advances led to the emergence of ionic liquids, which are excellent candidates as phase transfer catalysts. The inherent fine-tuning capability of these molecules, along with the potential of phase transfer catalytic reactions, epitomize the sustainable aspect of this field of research. Herein, a cohesive report of such applications will be presented, including the period from the last decade of the 20th century up to date. Full article
(This article belongs to the Special Issue The Influence of Phase Transfer Catalysis (PTC) in the Synthesis of Bioactive Compounds)
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