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Special Issue "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 2610

Special Issue Editors

Dr. Jolanta Jaśkowska
E-Mail Website
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
E-Mail Website
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

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2200 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 (3 papers)

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Research

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
Catalysts 2022, 12(10), 1236; https://doi.org/10.3390/catal12101236 - 14 Oct 2022
Viewed by 345
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
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Article
Regioselective Synthesis of Novel Functionalized Dihydro-1,4-thiaselenin-2-ylsufanyl Derivatives under Phase Transfer Catalysis
Catalysts 2022, 12(8), 889; https://doi.org/10.3390/catal12080889 - 12 Aug 2022
Cited by 1 | Viewed by 451
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
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Article
Mechanochemical Synthesis Method for Drugs Used in the Treatment of CNS Diseases under PTC Conditions
Catalysts 2022, 12(5), 464; https://doi.org/10.3390/catal12050464 - 21 Apr 2022
Cited by 2 | Viewed by 898
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
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