Journal Description
Organics
Organics
is an international, peer-reviewed, open access journal on organic chemistry published quarterly online by MDPI.
- Open Access— free for readers, with article processing charges (APC) paid by authors or their institutions.
- High Visibility: indexed within Scopus, ESCI (Web of Science), CAPlus / SciFinder, and other databases.
- Rapid Publication: manuscripts are peer-reviewed and a first decision is provided to authors approximately 41.3 days after submission; acceptance to publication is undertaken in 14.6 days (median values for papers published in this journal in the first half of 2024).
- Recognition of Reviewers: APC discount vouchers, optional signed peer review, and reviewer names published annually in the journal.
Impact Factor:
1.4 (2023);
5-Year Impact Factor:
1.5 (2023)
Latest Articles
Aromatic Functionalized Indanones and Indanols: Broad Spectrum Intermediates for Drug Candidate Diversification
Organics 2024, 5(3), 263-276; https://doi.org/10.3390/org5030014 - 1 Aug 2024
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A series of new aromatic substituted indanone and indanol building blocks have been prepared and are anticipated to aid future drug discovery studies. In total, seven compounds (7, 12–17) are expounded on, and all have been fully characterized.
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A series of new aromatic substituted indanone and indanol building blocks have been prepared and are anticipated to aid future drug discovery studies. In total, seven compounds (7, 12–17) are expounded on, and all have been fully characterized. In doing so, we have shown multiple examples of highly chemoselective reactions. One example employed an adaptation of Fujioka’s chemoselective reduction methodology, allowing an ester to be reduced in the presence of a ketone. In another example, an uncommon benzylic methyl group to aldehyde oxidation was demonstrated for two different compounds. These and other chemoselective interconversions allowed us to identify compound (12) as a remarkably flexible springboard for accessing a diverse array of indan-based building blocks (13–17).
Full article
Open AccessArticle
Synthesis and Properties of 3,8-Diaryl-2H-cyclohepta[b]furan-2-ones
by
Taku Shoji, Daichi Ando, Masayuki Iwabuchi, Tetsuo Okujima, Ryuta Sekiguchi and Shunji Ito
Organics 2024, 5(3), 252-262; https://doi.org/10.3390/org5030013 - 1 Aug 2024
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Synthesis of 3,8-diaryl-2H-cyclohepta[b]furan-2-ones was accomplished by the one-pot procedure involving sequential iodation and Suzuki–Miyaura coupling reactions. The optical and structural characteristics of 3,8-diaryl-2H-cyclohepta[b]furan-2-ones prepared were scrutinized using UV/Vis spectroscopy, theoretical calculations, and single-crystal X-ray crystallography.
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Synthesis of 3,8-diaryl-2H-cyclohepta[b]furan-2-ones was accomplished by the one-pot procedure involving sequential iodation and Suzuki–Miyaura coupling reactions. The optical and structural characteristics of 3,8-diaryl-2H-cyclohepta[b]furan-2-ones prepared were scrutinized using UV/Vis spectroscopy, theoretical calculations, and single-crystal X-ray crystallography. The redox properties of the compounds were also evaluated through cyclic voltammetry (CV) and differential pulse voltammetry (DPV). The findings reveal that the introduction of aryl groups at both the 3- and 8-positions significantly influences the electronic properties of the CHFs, resulting in distinct optical and electrochemical characteristics.
Full article
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Open AccessArticle
Unveiling the Relationship between Structure and Anticancer Properties of Permethylated Anigopreissin A: A Study with Thirteen Analogues
by
Ilaria Caivano, Alessandro Santarsiere, Mario Amati, Paolo Convertini, Maria Funicello, Paolo Lupattelli, Lucia Chiummiento and Anna Santarsiero
Organics 2024, 5(3), 237-251; https://doi.org/10.3390/org5030012 - 1 Aug 2024
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Permethylated anigopreissin A (PAA), a fully protected form of the natural anigopreissin A, was found in our previous study to be active against several cancer cells, up to IC50 0.24 μM for HepG2 cells. Herein, a total of thirteen PAA analogues with variations
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Permethylated anigopreissin A (PAA), a fully protected form of the natural anigopreissin A, was found in our previous study to be active against several cancer cells, up to IC50 0.24 μM for HepG2 cells. Herein, a total of thirteen PAA analogues with variations in the number, position of substituents and unsaturation were synthesised starting from a common precursor, and their ability to induce cell growth inhibition was tested. By comparing the antiproliferative effect of the analogues with PAA and with the help of computational studies, we have gained valuable insights into both the biological activity and structure of this natural class of compounds. Indeed, we discovered the importance of the C-3 ring in modulating the biological activity of PAA, as well as the crucial role of the trans configuration of the styryl double bond and the significance of substitutions on the other parts of the molecule.
Full article
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Graphical abstract
Open AccessReview
Lewis Acid-Initiated Ring-Opening Reactions of Five- and Six-Membered Cyclic Ethers Based on the Oxonium Ylide Intermediates
by
Dandan Jiang, Jun Xiao, Yingzhen Zhang, Kunming Liu, Juanhua Li and Jinbiao Liu
Organics 2024, 5(3), 219-236; https://doi.org/10.3390/org5030011 - 22 Jul 2024
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In light of the small ring strain of five/six-membered cyclic ethers, constructing complex molecules via ring-opening reactions has consistently been a highly challenging topic in organic synthesis. Induced by Lewis acids, the charge redistribution in cyclic ethers forms oxonium ylide intermediates, thereby activating
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In light of the small ring strain of five/six-membered cyclic ethers, constructing complex molecules via ring-opening reactions has consistently been a highly challenging topic in organic synthesis. Induced by Lewis acids, the charge redistribution in cyclic ethers forms oxonium ylide intermediates, thereby activating the C–O bond and subsequently facilitating nucleophilic attack for ring opening. In recent years, a variety of novel Lewis acids, encompassing those with new metal centers and frustrated Lewis pairs (FLPs), have been effectively utilized to induce the formation of oxonium ylides, offering a diverse array of methods for the ring opening of five/six-membered cyclic ethers. This review conveys the extensive application advancements of diverse Lewis acid types for cyclic ether ring-opening reactions over the past two decades, originating from the perspective of the classification of Lewis acids. Furthermore, the substrate applicability and chemical transformation efficiency of these Lewis acids in the ring-opening reactions of cyclic ethers have also been discussed herein.
Full article
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Scheme 1
Open AccessArticle
Spontaneous Formation of Strained Anti-Bredt Bridgehead Alkenes upon Computational GeometryOptimization of Bicyclic β-Halo Carbanions
by
Gary W. Breton and Jazmine V. Ridlehoover
Organics 2024, 5(3), 205-218; https://doi.org/10.3390/org5030010 - 5 Jul 2024
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Bridgehead alkenes are polycyclic molecules bearing at least one C=C bond that includes a bridgehead carbon atom. For small bicyclic systems, these bonds are highly strained due to geometric constraints placed on the sp2 hybridized carbon atoms. These small, strained molecules have
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Bridgehead alkenes are polycyclic molecules bearing at least one C=C bond that includes a bridgehead carbon atom. For small bicyclic systems, these bonds are highly strained due to geometric constraints placed on the sp2 hybridized carbon atoms. These small, strained molecules have been termed “anti-Bredt” alkenes. β-halo carbanions have served as convenient precursors to bridgehead alkenes in experimental studies. We observed that upon attempted computational geometric optimizations (ωB97X-D/aug-cc-pVDZ) of the precursors, spontaneous elimination of the halide occurs along with formation of the anti-Bredt alkene in many cases. Such computational eliminations were shown to faithfully mimic experimentally obtained results. Computational elimination was not observed for [1.1.1] or [2.1.1] frameworks, in agreement with predictions that these bridgehead alkenes are too strained to be formed. However, computational elimination from the [2.2.1] framework was observed to form 1-norbornene, a compound suggested in experimental work to be a reactive intermediate. Similarly, [3.1.1] frameworks and higher led to eliminations upon computational geometric optimization, in agreement with experimental findings. Natural bond order (NBO) calculations of the starting geometries proved to be excellent predictors as to whether elimination would take place. Those precursor compounds exhibiting delocalization energies in the order of 10 kcal/mol between the lone-pair electrons of the carbon atom and σ*C-Br were generally found to undergo elimination. Thus, computational optimization of β-halo substituted bicyclic precursor anions can be used to predict whether strained anti-Bredt alkenes are likely to be formed, thereby saving valuable time and costs in the experimental lab.
Full article
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Open AccessReview
Chiral Nonaromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation
by
Mario Orena and Samuele Rinaldi
Organics 2024, 5(3), 163-204; https://doi.org/10.3390/org5030009 - 2 Jul 2024
Abstract
This review deals with the functionalization of double bonds carried out in the presence of a chiral catalyst exploiting the intramolecular attack to haliranium ions by nucleophilic nitrogen of amides or carbamates prepared from achiral aminoalkenes, and the C–N bonds formation leads to
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This review deals with the functionalization of double bonds carried out in the presence of a chiral catalyst exploiting the intramolecular attack to haliranium ions by nucleophilic nitrogen of amides or carbamates prepared from achiral aminoalkenes, and the C–N bonds formation leads to highly enantioenriched nonaromatic heterocycles. A range of protocols are reported, emphasizing the synthesis of many natural and biologically active products of pharmacological interest prepared according to this methodology.
Full article
(This article belongs to the Special Issue Heterocyclic Compounds and Their Derivatives: Synthesis and Applications)
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Open AccessReview
Architecture of Molecular Logic Gates: From Design to Application as Optical Detection Devices
by
Gleiston G. Dias and Francielly T. Souto
Organics 2024, 5(2), 114-162; https://doi.org/10.3390/org5020008 - 6 Jun 2024
Cited by 1
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Three decades after A. P. de Silva’s seminal paper introduced the concept of logic gates at the molecular level, the field of molecular logic gates (MLGs) has witnessed significant advancements. MLGs are devices designed to perform logical operations, utilizing one or more physical
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Three decades after A. P. de Silva’s seminal paper introduced the concept of logic gates at the molecular level, the field of molecular logic gates (MLGs) has witnessed significant advancements. MLGs are devices designed to perform logical operations, utilizing one or more physical or chemical stimulus signals (inputs) to generate an output response. Notably, MLGs have found diverse applications, with optical detection of analytes emerging as a notable evolution of traditional chemosensors. Organic synthesis methods are pivotal in crafting molecular architectures tailored as optical devices capable of analyte detection through logical functions. This review delves into the fundamental aspects and physical–chemical properties of MLGs, with a particular emphasis on synthetic strategies driving their design.
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Open AccessEditorial
Special Issue “Progress in Synthesis and Applications of Phosphorus-Containing Compounds”
by
Tomasz K. Olszewski
Organics 2024, 5(2), 111-113; https://doi.org/10.3390/org5020007 - 27 May 2024
Abstract
Organophosphorus compounds, due to their interesting physicochemical properties, have found wide applications in many important areas of the chemical industry, such as the synthesis of utility chemicals [...]
Full article
(This article belongs to the Special Issue Progress in Synthesis and Applications of Phosphorus-Containing Compounds)
Open AccessReview
How Much Potential Do Nucleoside Analogs Offer to Combat Human Corona Viruses?
by
Włodzimierz Buchowicz and Mariola Koszytkowska-Stawińska
Organics 2024, 5(2), 71-110; https://doi.org/10.3390/org5020006 - 8 May 2024
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Nucleoside analogs (NAs) have been extensively examined as plausible antiviral agents in recent years, in particular since the outbreak of the global pandemic of COVID-19 in 2019. In this review, the structures and antiviral properties of over 450 NAs are collected according to
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Nucleoside analogs (NAs) have been extensively examined as plausible antiviral agents in recent years, in particular since the outbreak of the global pandemic of COVID-19 in 2019. In this review, the structures and antiviral properties of over 450 NAs are collected according to the type of virus, namely SARS-CoV, SARS-CoV-2, MERS-CoV, HCoV-OC43, HCoV-229E, and HCoV-NL63. The activity of the NAs against HCoV-related enzymes is also presented. Selected studies dealing with the mode of action of the NAs are discussed in detail. The repurposing of known NAs appears to be the most extensively investigated scientific approach towards efficacious anti-HCoV agents. The recently reported de novo-designed NAs seem to open up additional approaches to new drug candidates.
Full article
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Open AccessArticle
Innovative Application of Polyether Amine as a Recyclable Catalyst in Aerobic Thiophenol Oxidation
by
Lingxia Chen, Junyu Li, Ke Ni, Xinshu Qin, Lijun Wang, Jiaman Hou, Chao Wang, Xuan Li, Minlong Wang and Jie An
Organics 2024, 5(2), 59-70; https://doi.org/10.3390/org5020005 - 26 Apr 2024
Cited by 1
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Polyether amines are versatile compounds characterized by a flexible structure, consisting of polyoxypropylene and polyoxyethylene as the backbone, with amine groups at each end. They have widespread applications in various industrial processes and daily life. Despite their versatility, the utilization of polyether amines
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Polyether amines are versatile compounds characterized by a flexible structure, consisting of polyoxypropylene and polyoxyethylene as the backbone, with amine groups at each end. They have widespread applications in various industrial processes and daily life. Despite their versatility, the utilization of polyether amines as base catalysts is rare. In this study, one kind of three-arm polyether amine 1 was employed as an environmentally friendly, cost-effective catalyst for the aerobic oxidation of thiophenols, leading to the synthesis of disulfides. The oxidative coupling of thiols serves as a fundamental pathway for the production of disulfides, which are vital in both chemical and biological processes. In contrast to known methods for thiol oxidation, this polyether amine-based catalytic process eliminates the need for expensive stoichiometric oxidants and minimizes the formation of over-oxidized by-products. Using a mere 0.5 mol % of the polyether amine 1 as the catalyst, a remarkable > 96% yield was achieved for all 16 tested substrates, encompassing a diverse range of functional groups, under the catalytic aerobic oxidation conditions. Furthermore, it is noteworthy that over 90% of the polyether amine catalyst can be efficiently recovered for reuse without loss of activity, making this a sustainable and cost-effective catalytic approach.
Full article
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Open AccessArticle
Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile
by
Zhao-Hua Chen, Shi-Wei Yu, Wen-Jin Xu, Miao-Xin Li, Yong Zeng, Si-Wei Deng, Jian-Yun Lin and Zhao-Yang Wang
Organics 2024, 5(2), 46-58; https://doi.org/10.3390/org5020004 - 2 Apr 2024
Cited by 2
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Recently, the construction of the trisubstituted olefin-type probe molecules has elicited the attention of many researchers. However, the synthesis of the trisubstituted olefin-type probes containing two N-heterocycles simultaneously has been rarely reported. In this study, starting from the inexpensive mucobromic acid 1
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Recently, the construction of the trisubstituted olefin-type probe molecules has elicited the attention of many researchers. However, the synthesis of the trisubstituted olefin-type probes containing two N-heterocycles simultaneously has been rarely reported. In this study, starting from the inexpensive mucobromic acid 1 and N-heterocyclic compound 2, we first utilized a simple one-step reaction to synthesize a series of trisubstituted olefin-type compounds 3 simultaneously bearing with the structure of two N-heterocyclic rings in the absence of transition metal catalysts with a yield of 62–86%. The optimal reaction conditions were systematically explored, and the structure of the obtained compounds 3 were well characterized with 1H NMR, 13C NMR, X-ray single-crystal and HR-MS. The preliminary observation showed that, in the presence of base, mucobromic acid 1 reacts as its ring-opening structure, and the successive nucleophilic substitution reaction and Michael addition reaction can generate the target product 3. Considering that the aldehyde group in the molecular structure of the trisubstituted olefin-type compounds 3 may react with malononitrile, we carried out some relevant investigations so as to realize the visual detection of malononitrile. Interestingly, among the products, compounds 3a–3c can be prepared in portable test strips through a simple process and used to achieve the naked-eye detection of malononitrile in environmental systems as designed.
Full article
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Graphical abstract
Open AccessArticle
Supramolecular Catalysis with Chiral Mono- and Bis-(Thio)Urea-Derivatives
by
Veronica Iuliano, Paolo Della Sala, Carmen Talotta, Margherita De Rosa, Carmine Gaeta, Placido Neri and Annunziata Soriente
Organics 2024, 5(2), 32-45; https://doi.org/10.3390/org5020003 - 26 Mar 2024
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Chiral mono- and bis-(thio)urea supramolecular organocatalysts were studied in the enantioselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF) to carbonylic compounds; the corresponding chiral γ-hydroxymethyl-butenolides are obtained in good yields and with high enantiomeric excesses. The catalyst structure, as well as the reaction conditions,
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Chiral mono- and bis-(thio)urea supramolecular organocatalysts were studied in the enantioselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF) to carbonylic compounds; the corresponding chiral γ-hydroxymethyl-butenolides are obtained in good yields and with high enantiomeric excesses. The catalyst structure, as well as the reaction conditions, strongly influence the efficiency of the reaction. The conformational features of mono(thio)urea catalysts 2 and 3 and bis(thio)urea catalysts 7 and 8 were investigated by DFT calculations along with the structure of their complexes with benzaldehyde. Natural Bond Orbital (NBO) and Non-Covalent Interaction (NCI) calculations provided useful information concerning the activating H-bonding interactions in the complexes.
Full article
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Open AccessArticle
Synthesis and Butyllithium-Induced Cyclisation of 2-Benzyloxyphenylphosphonamidates Giving 2,3-Dihydrobenzo[d][1,3]oxaphospholes
by
R. Alan Aitken, Khadija Ait Moulay, David B. Cordes, Ryan A. Inwood, Fraser G. Jamieson, Alexander J. B. Nelson and Aidan P. McKay
Organics 2024, 5(1), 12-31; https://doi.org/10.3390/org5010002 - 1 Feb 2024
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A series of fourteen O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the ortho position was prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, they underwent cyclisation in eight cases to give the novel 2,3-dihydrobenzo[d][1,3]oxaphospholes
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A series of fourteen O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the ortho position was prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, they underwent cyclisation in eight cases to give the novel 2,3-dihydrobenzo[d][1,3]oxaphospholes in moderate to low yield as a single diastereomer, for which the relative configuration was determined by X-ray diffraction in one case.
Full article
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Graphical abstract
Open AccessArticle
How an Internal Supramolecular Interaction Determines the Stereochemistry of a Metal Center
by
Maxime Steinmetz, Christophe Gourlaouen and David Sémeril
Organics 2024, 5(1), 1-11; https://doi.org/10.3390/org5010001 - 4 Jan 2024
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The chloro-P,N-{diphenylphosphanyl-[(5-phenyl-1,3,4-oxadiazol-2-ylamino)phenyl-me- thyl]}(p-cymene)ruthenium(II) hexafluorophosphate complex (4) was obtained in two steps from diphenylphosphanyl-[(5-phenyl-1,3,4-oxadiazol-2-ylamino)phenyl-methyl] borane (2). In the first step, the oxadiazole ring coordinated with the ruthenium atom, resulting in the formation of the
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The chloro-P,N-{diphenylphosphanyl-[(5-phenyl-1,3,4-oxadiazol-2-ylamino)phenyl-me- thyl]}(p-cymene)ruthenium(II) hexafluorophosphate complex (4) was obtained in two steps from diphenylphosphanyl-[(5-phenyl-1,3,4-oxadiazol-2-ylamino)phenyl-methyl] borane (2). In the first step, the oxadiazole ring coordinated with the ruthenium atom, resulting in the formation of the dichloro-N-{diphenylphosphanyl-[(5-phenyl-1,3,4-oxadiazol-2-ylamino)phenyl-methyl]borane}(p-cymene) ruthenium(II) complex (3). During the crystallization of the P,N-chelate ruthenium complex, the formation of conglomerate crystals was revealed by X-ray structure analysis. Only two stereoisomers were obtained with (S)-Ru and (R)-C configurations in the first complex and with (R)-Ru and (S)-C configurations in the second. This deracemization during crystallization is due to the formation of a hydrogen bond between the P,N-ligand and the chlorine atom (CH•••Cl). This supramolecular interaction allows the transfer of the ligand chirality to the metal center and decrees the stereochemistry of the ruthenium atom.
Full article
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Graphical abstract
Open AccessReview
4-Hydroxy-2-pyrones: Synthesis, Natural Products, and Application
by
Vladislav V. Fedin, Dmitrii L. Obydennov, Sergei A. Usachev and Vyacheslav Y. Sosnovskikh
Organics 2023, 4(4), 539-561; https://doi.org/10.3390/org4040037 - 15 Dec 2023
Abstract
4-Hydroxy-2-pyrones are of interest as potential biorenewable molecules for a sustainable transition from biomass feedstock to valuable chemical products. This review focuses on the methodologies for the synthesis of 4-hydroxy-2-pyrones published over the last 20 years. These pyrones as polyketides are widespread in
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4-Hydroxy-2-pyrones are of interest as potential biorenewable molecules for a sustainable transition from biomass feedstock to valuable chemical products. This review focuses on the methodologies for the synthesis of 4-hydroxy-2-pyrones published over the last 20 years. These pyrones as polyketides are widespread in Nature and possess versatile bioactivity that makes them an attractive target for synthesis and modification. Biosynthetic paths of the pyrones are actively developed and used as biotechnological approaches for the construction of natural and unnatural polysubstituted 4-hydroxy-2-pyrones. The major synthetical methods are biomimetic and are based on the cyclization of tricarbonyl compounds. Novel chemical methods of de novo synthesis based on alkyne cyclizations using transition metal complexes and ketene transformations allow for straightforward access to 4-hydroxy-2-pyrones and have been applied for the construction of natural products. Possible directions for further pyrone ring modification are discussed.
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(This article belongs to the Special Issue The Modern Trends in Organic Synthesis, including PASE and Green Chemistry)
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Open AccessReview
Synthesis of 2-Substituted Benzimidazole Derivatives as a Platform for the Development of UV Filters and Radical Scavengers in Sunscreens
by
Kameliya K. Anichina and Nikolai I. Georgiev
Organics 2023, 4(4), 524-538; https://doi.org/10.3390/org4040036 - 28 Nov 2023
Cited by 1
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The modern trend in sunscreen products is towards the development of UV filters with multi-functional properties, to provide a broad shielding against ultraviolet radiation, antioxidant activity, and the prevention of skin cancer. Additionally, they should also be safe for humans as well as
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The modern trend in sunscreen products is towards the development of UV filters with multi-functional properties, to provide a broad shielding against ultraviolet radiation, antioxidant activity, and the prevention of skin cancer. Additionally, they should also be safe for humans as well as the environment. The benzimidazole heterocycle is a suitable platform for the development of such multifunctional molecules with potential application in cosmetic formulations, due to their ability to act as both UV protectors and reactive pharmacophores. This review presents for the first time the progress in the synthesis and optimization of benzimidazole compounds as UV sunscreen filters. The modifications to the substitution pattern of the lead compound and structure–activity relationships are discussed, as well as the synthetic approaches for the preparation of 2-substituted benzimidazoles. These aggregated data will be useful in future in the development of modern benzimidazole-based sunscreen.
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Graphical abstract
Open AccessReview
Synthesis of Antifungal Heterocycle-Containing Mannich Bases: A Comprehensive Review
by
Diego Quiroga and Ericsson Coy-Barrera
Organics 2023, 4(4), 503-523; https://doi.org/10.3390/org4040035 - 9 Nov 2023
Cited by 2
Abstract
Mannich bases are a class of organic compounds usually obtained by the condensation reaction between an amine, a compound with active hydrogens, and an aldehyde. They are versatile intermediates in organic synthesis, and those compounds containing this motif find applications in pharmaceutical, agrochemical,
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Mannich bases are a class of organic compounds usually obtained by the condensation reaction between an amine, a compound with active hydrogens, and an aldehyde. They are versatile intermediates in organic synthesis, and those compounds containing this motif find applications in pharmaceutical, agrochemical, and even material fields since they are widely known for their wide range of biological activities, including antimicrobial properties. Thus, as part of our interest in antifungal agents, this narrative review aimed to gather information from the literature on the synthesis of various representative Mannich-base-containing compounds, particularly centered on those exhibiting antifungal properties. In this context, the compilation indicated that Mannich bases could be considered as a relevant toxophore/pharmacophore by incorporating heterocyclic moieties to be implemented for the design of new antifungal agents, given its proven efficacy against phytopathogens, other opportunistic human pathogens, and some dermatophytic fungal species, which can be further exploited as agrochemical agents or in medicinal applications to treat fungal infections. The antifungal effect exhibited by Mannich bases conjugated with oxa and/or aza-heterocycles suggests that compounds that have a heterocyclic system attached to the β-amino core are attractive alternatives oriented to the synthesis of novel and helpful antifungal agents.
Full article
(This article belongs to the Special Issue Heterocyclic Compounds and Their Derivatives: Synthesis and Applications)
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Open AccessArticle
Absorption Spectra of Protonated Corroles: Two Distinct Patterns Due to Peripheral Substitution Architecture
by
Lev L. Gladkov, Dmitry V. Klenitsky and Mikalai M. Kruk
Organics 2023, 4(4), 490-502; https://doi.org/10.3390/org4040034 - 9 Oct 2023
Cited by 1
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The origin of individual features in the ground state absorption spectra of two protonated corroles differing in the architecture of peripheral substitution (either Cm-aryl or Cb-alkyl) have been studied in detail with the ground state absorption spectroscopy and density
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The origin of individual features in the ground state absorption spectra of two protonated corroles differing in the architecture of peripheral substitution (either Cm-aryl or Cb-alkyl) have been studied in detail with the ground state absorption spectroscopy and density functional theory calculations. The geometry optimization, molecular orbitals and absorption spectra calculation have been carried out. It was found that protonation leads to the saddle type macrocycle conformation in contrast with the wave type conformation known for the parent-free base corroles. The mean plane deviation parameter Δ23 for the macrocycle, pyrrole tilting angles and the degree of pyramidalization λ2 of all four pyrrole nitrogens was found to depend on the peripheral substitution architecture. Macrocycle conformation of the protonated forms has distinct asymmetrical features which are reflected by the sets of values of the tilting angles and values of pyramidalization degree. The pair of pyrroles B and C has smaller tilting angles and higher pyramidalization degree values, whereas the opposite trend was found for the pair of pyrroles A and D. Electronic effects and structural differences induced by substitution lead to the pronounced shifts of the molecular orbitals. In the Cb-alkylated corrole, almost-degenerated HOMO and HOMO-1 molecular orbitals lead to enhancement of the configuration interaction. As a result, the Qx transition oscillator strength goes down, becoming comparable to that of the Qy one. A large HOMO-HUMO-1gap in the Cm-aryl corrole minimizes the configuration interaction, giving rise to Qx band domination in the visible range spectrum.
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Recent Advances in Application of Alkoxy Radical in Organic Synthesis
by
Munsaf Ali, Shi Sewell, Juncheng Li and Ting Wang
Organics 2023, 4(4), 459-489; https://doi.org/10.3390/org4040033 - 28 Sep 2023
Abstract
Alkoxy radicals have been identified as versatile intermediates in synthetic chemistry in the last few decades. Over the last decade, various catalytic processes for the in situ generation of alkoxy radicals have been explored, leading to the development of new synthetic methodologies based
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Alkoxy radicals have been identified as versatile intermediates in synthetic chemistry in the last few decades. Over the last decade, various catalytic processes for the in situ generation of alkoxy radicals have been explored, leading to the development of new synthetic methodologies based on alkoxy radicals. In this review, we provided a comprehensive review of recent developments in the utilization of alkoxy radicals in diverse organic transformations, natural product synthesis, and the late-stage modification of bioactive molecules through the implementation of the photoredox methodology.
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(This article belongs to the Special Issue Design and Development of New Organic Synthetic Methods and Techniques)
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Open AccessArticle
Stimuli-Sensitive Pyrenylated Hydrogels as Optical Sensing Platform for Multiple Metal Ions
by
Dipen Biswakarma, Nilanjan Dey and Santanu Bhattacharya
Organics 2023, 4(3), 447-458; https://doi.org/10.3390/org4030032 - 4 Sep 2023
Abstract
In the present work, we report a thermoresponsive hydrogel formed by the self-assembly of compounds 1 and 2 Milli Q water. Both hydrogels showed thixotropic behavior. Atomic force microscopy (AFM) studies confirm the fiber-like microstructure of compounds 1 and 2, but denser fibers
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In the present work, we report a thermoresponsive hydrogel formed by the self-assembly of compounds 1 and 2 Milli Q water. Both hydrogels showed thixotropic behavior. Atomic force microscopy (AFM) studies confirm the fiber-like microstructure of compounds 1 and 2, but denser fibers were observed in the case of compound 1. The hydrogel formed by compound 1 detected Cu2+, Fe3+, and Hg2+, whereas the hydrogel of 2 showed a change in the optical signal, specifically upon adding Cu2+ and Hg2+. Mechanistically, adding metal ions to the hydrogel resulted in the formation of a (1:1) complex with Fe3+ and Hg2+ and (2:1) with Cu2+. The detection of metal ions has also been achieved in real-life samples, such as in tap water. Low-cost portable gel-coated paper strips have also been developed for the onsite detection of these metal ions.
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(This article belongs to the Special Issue Aromatic Heterocycles: A Wonderful Pool of Organic Materials)
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