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Green Approaches in Organic Chemistry

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Green Chemistry".

Deadline for manuscript submissions: closed (30 September 2022) | Viewed by 7766

Special Issue Editor

Special Issue Information

Dear Colleagues,

This Special Issue is open for all kinds of green aspects in organic chemistry, applied organic chemistry, as well as industrial organic chemistry including the pharmaceutical–fine chemical and plastic industry.

In addition to atomic efficient transformations, catalytic reactions are especially important in the field, including heterogeneous and homogeneous accomplishments, as well as the development of new metal and metal-free catalysts and P-ligands, phase transfer catalysis, and selectivity issues, such as chemo-, regio-, diastereo-, and enantioselectivity. The application of green solvents, or solvent-free reactions is also in the scope of the Special Issue. Ionic liquids may be used as solvents or catalysts/additives. Microwave-assisted or sonochemically promoted reactions are also welcome, as well as flow chemical accomplishments. Green technologies in the pharmaceutical industry are also potential topics. All kinds of papers, including original research and review manuscripts, are invited.

Prof. Dr. György Keglevich
Guest Editor

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. Molecules is an international peer-reviewed open access semimonthly 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

  • green chemistry
  • catalytic transformations
  • P-ligands
  • phase transfer catalysis
  • selectivity
  • solvent-free reactions
  • ionic liquids
  • microwaves
  • sonochemistry
  • flow chemistry

Published Papers (5 papers)

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Research

26 pages, 7854 KiB  
Article
Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation
by Daniel Swoboda, Jacek E. Nycz, Nataliya Karaush-Karmazin, Boris Minaev, Maria Książek, Joachim Kusz and Radosław Podsiadły
Molecules 2022, 27(21), 7519; https://doi.org/10.3390/molecules27217519 - 04 Nov 2022
Cited by 2 | Viewed by 1753
Abstract
Two unique structures were isolated from the phosphorylation reaction of 10H-phenothiazine. The 5,5-dimethyl-2-(10H-phenothiazin-10-yl)-1,3,2-dioxaphosphinane 2-oxide (2a) illustrates the product of N-phosphorylation of phenothiazine. Moreover, a potential product of 2a instability, a thiophosphoric acid 2b, was successfully [...] Read more.
Two unique structures were isolated from the phosphorylation reaction of 10H-phenothiazine. The 5,5-dimethyl-2-(10H-phenothiazin-10-yl)-1,3,2-dioxaphosphinane 2-oxide (2a) illustrates the product of N-phosphorylation of phenothiazine. Moreover, a potential product of 2a instability, a thiophosphoric acid 2b, was successfully isolated and structurally characterized. Molecule 2a, similarly to sulfoxide derivative 3, possesses interesting phosphorescence properties due to the presence of d-pπ bonds. The X-ray, NMR, and DFT computational studies indicate that compound 2a exhibits an anomeric effect. Additionally, the syntheses of selected symmetrical and unsymmetrical pyridine-embedded phenazines were elaborated. To compare the influence of phosphorus and sulfur atoms on the structural characteristics of 10H-phenothiazine derivatives, the high-quality crystals of (4a,12a-dihydro-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxalin-12-yl)(phenyl)methanone (1) and selected phenazines 5,12-diisopropyl-3,10-dimethyldipyrido[3,2-a:3′,2′-h]phenazine (5) and 5-isopropyl-N,N,3-trimethylpyrido[3,2-a]phenazin-10-amine (6a) were obtained. The structures of molecules 1, 2a, 2-mercapto-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (2b), 3,7-dinitro-10H-phenothiazine 5-oxide (3), 5 and 6a were determined by single-crystal X-ray diffraction measurements. Full article
(This article belongs to the Special Issue Green Approaches in Organic Chemistry)
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12 pages, 7727 KiB  
Article
“One-Pot” CuCl2-Mediated Condensation/C–S Bond Coupling Reactions to Synthesize Dibenzothiazepines by Bi-Functional-Reagent N, N′-Dimethylethane-1,2-Diamine
by Dehe Wang, Qichao Lu, Zhanjun Li, Chen Fang, Ran Liu, Bingchuan Yang and Guodong Shen
Molecules 2022, 27(21), 7392; https://doi.org/10.3390/molecules27217392 - 31 Oct 2022
Cited by 1 | Viewed by 999
Abstract
The efficient “One-pot” CuCl2-catalyzed C–S bond coupling reactions were developed for the synthesis of dibenzo[b,f][1,4]thiazepines and 11-methy-ldibenzo[b,f][1,4]thiazepines via 2-iodobenzaldehydes/2-iodoacetophenones with 2-aminobenzenethiols/2,2′-disulfanediyldianilines by using bifunctional-reagent N, N′-dimethylethane-1,2-diamine (DMEDA), which worked as ligand and reductant. [...] Read more.
The efficient “One-pot” CuCl2-catalyzed C–S bond coupling reactions were developed for the synthesis of dibenzo[b,f][1,4]thiazepines and 11-methy-ldibenzo[b,f][1,4]thiazepines via 2-iodobenzaldehydes/2-iodoacetophenones with 2-aminobenzenethiols/2,2′-disulfanediyldianilines by using bifunctional-reagent N, N′-dimethylethane-1,2-diamine (DMEDA), which worked as ligand and reductant. The reactions were compatible with a range of substrates to give the corresponding products in moderate to excellent yields. Full article
(This article belongs to the Special Issue Green Approaches in Organic Chemistry)
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8 pages, 2370 KiB  
Article
A Green Chemical Approach for Iodination of Pyrimidine Derivatives by Mechanical Grinding under Solvent-Free Conditions
by Thananjeyan Balasubramaniyam, Byeong-Seon Kim, Badvel Pallavi, Ho-Seong Jin, Sung Kuk Kim and Joon-Hwa Lee
Molecules 2022, 27(19), 6386; https://doi.org/10.3390/molecules27196386 - 27 Sep 2022
Cited by 1 | Viewed by 1468
Abstract
The iodination of pyrimidines is usually carried out by using toxic reagents under acidic conditions, such as with sulfuric acid and nitric acid. To avoid toxic reagents, we developed a simple and eco-friendly approach for the iodination of pyrimidine derivatives under solvent-free conditions [...] Read more.
The iodination of pyrimidines is usually carried out by using toxic reagents under acidic conditions, such as with sulfuric acid and nitric acid. To avoid toxic reagents, we developed a simple and eco-friendly approach for the iodination of pyrimidine derivatives under solvent-free conditions using solid iodine and AgNO3 as an electrophilic iodinating reagent. The advantages of this method are the relatively short reaction time (20–30 min), simple set-up procedure, high yields (70–98%), and environmentally friendly reaction conditions. Our novel approach for the iodination of pyrimidines, as well as a variety of their derivatives, will contribute to the development of nucleobase-related drug candidates. Full article
(This article belongs to the Special Issue Green Approaches in Organic Chemistry)
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9 pages, 1678 KiB  
Article
A Study on the Direct Esterification of Monoalkylphosphates and Dialkylphosphates; The Conversion of the Latter Species to Trialkylphosphates by Alkylating Esterification
by Péter Ábrányi-Balogh, Nikoletta Harsági, László Drahos and György Keglevich
Molecules 2022, 27(15), 4674; https://doi.org/10.3390/molecules27154674 - 22 Jul 2022
Cited by 2 | Viewed by 1104
Abstract
The microwave (MW)-assisted direct esterification of certain P-acids is a green method. Quantum chemical calculations revealed that the activation enthalpy (ΔH#) for the exothermic monoalkylphosphate → dialkylphosphate transformation was on the average 156.6 kJ mol−1, while ΔH [...] Read more.
The microwave (MW)-assisted direct esterification of certain P-acids is a green method. Quantum chemical calculations revealed that the activation enthalpy (ΔH#) for the exothermic monoalkylphosphate → dialkylphosphate transformation was on the average 156.6 kJ mol−1, while ΔH# for the dialkylphosphate → trialkylphosphate conversion was somewhat higher, 171.2 kJ mol−1, and the energetics of the elemental steps of this esterification was less favorable. The direct monoesterification may be performed on MW irradiation in the presence of a suitable ionic liquid additive. However, the second step, with the less favorable energetics as a whole, could not be promoted by MWs. Hence, dialkylphosphates had to be converted to triesters by another method that was alkylation. In this way, it was also possible to synthesize triesters with different alkyl groups. Eventually a green, P-chloride free MW-promoted two-step method was elaborated for the synthesis of phosphate triesters. Full article
(This article belongs to the Special Issue Green Approaches in Organic Chemistry)
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16 pages, 1877 KiB  
Article
Efficient Synthesis of Acylated, Dialkyl α-Hydroxy-Benzylphosphonates and Their Anticancer Activity
by Petra R. Varga, Alexandra Belovics, Péter Bagi, Szilárd Tóth, Gergely Szakács, Szilvia Bősze, Rita Szabó, László Drahos and György Keglevich
Molecules 2022, 27(7), 2067; https://doi.org/10.3390/molecules27072067 - 23 Mar 2022
Cited by 4 | Viewed by 1781
Abstract
An efficient method applying acyl chlorides as reagents was developed for the acylation of the hindered hydroxy group of dialkyl α-hydroxy-benzylphosphonates. The procedure did not require any catalyst. A few acylations were also performed with the SC-enantiomer of dimethyl α-hydroxy-benzylphosphonate, and [...] Read more.
An efficient method applying acyl chlorides as reagents was developed for the acylation of the hindered hydroxy group of dialkyl α-hydroxy-benzylphosphonates. The procedure did not require any catalyst. A few acylations were also performed with the SC-enantiomer of dimethyl α-hydroxy-benzylphosphonate, and the optical purity was retained. A part of the acyloxyphosphonates was tested against eight tumor cell lines of different tissue origin at c = 50 μM concentration. The compounds elicited moderate cytostatic effect against breast, skin, prostate, colon, and lung carcinomas; a melanoma cell line; and against Kaposi’s sarcoma cell lines. Then, dose-dependent cytotoxicity was assayed, and benzoylation of the α-hydroxy group was identified as a moiety that increases anticancer cytotoxicity across all cell lines. Surprisingly, a few analogues were more toxic to multidrug resistant cancer cell lines, thus evading P-glycoprotein mediated drug extrusion. Full article
(This article belongs to the Special Issue Green Approaches in Organic Chemistry)
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