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
Amphiphilic Fluorescein Triazoles: Synthesis and Visible-Light Catalysis in Water
Organics 2024, 5(3), 346-360; https://doi.org/10.3390/org5030018 - 11 Sep 2024
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Triazole derivatives of fluorescein-containing N,N-dimethylaminopropyl fragments and their ammonium salts were synthesized with yields of 74–85%. The resulting compounds exhibit fluorescent properties in the green region of the visible spectrum. The critical aggregation concentration (CAC) was estimated using a pyrene
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Triazole derivatives of fluorescein-containing N,N-dimethylaminopropyl fragments and their ammonium salts were synthesized with yields of 74–85%. The resulting compounds exhibit fluorescent properties in the green region of the visible spectrum. The critical aggregation concentration (CAC) was estimated using a pyrene fluorescent probe corresponding to a range of 0.28–1.43 mM, and at concentrations above the CAC, the compounds form stable aggregates ranging from 165 to 202 nm. A relative quantum yield of 5–24% has been calculated based on fluorescence and UV spectra. The best value is shown by a derivative containing a tetradecyl substituent. When studying the photocatalytic properties of synthesized compounds through the reaction between N-substituted 1,2,3,4-tetrahydroisoquinoline and malonic ester, the mono-tetradecyl derivative demonstrated the best results. According to gas chromatography–mass spectrometry (GC-MS) data, the conversion of the initial heterocycle reached 95%. Therefore, these resulting compounds have the potential to act as an effective photocatalysts.
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Open AccessReview
A Review on Barbituric Acid and Its Derivatives: Synthesis, Reactions, and Bio-Applications
by
Navneet Kaur, Manvinder Kaur, Harvinder Singh Sohal, Haesook Han and Pradip K. Bhowmik
Organics 2024, 5(3), 298-345; https://doi.org/10.3390/org5030017 - 5 Sep 2024
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Barbituric acid is a heterocyclic compound with various pharmacological and biological applications. This review paper provides a comprehensive overview of barbituric acid’s synthesis, reactions, and bio-applications, highlighting its multifaceted role in various fields. Many heterocyclic derivatives were formed based on barbituric acid, for
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Barbituric acid is a heterocyclic compound with various pharmacological and biological applications. This review paper provides a comprehensive overview of barbituric acid’s synthesis, reactions, and bio-applications, highlighting its multifaceted role in various fields. Many heterocyclic derivatives were formed based on barbituric acid, for instance, pyrano-fused pyrimidine derivatives, spiro-oxindole derivatives, chrome-based barbituric acid derivatives, and many more via the atom economic method, Michael addition reaction, Knoevenagel condensation reaction, etc. In the context of bio-applications, this review examines the production of a wide range of bioactive drugs like anti-histamine, anti-leprotic, sedative–hypnotic, anti-inflammatory, anti-urease, antiviral, anti-AIDS, antimicrobial, antioxidant, anticonvulsant, anesthetic agent, antitumor, and anticancer drugs using efficient multicomponent reactions. By showcasing the versatility and potential of this compound, it aims to inspire further research and innovation in the field, leading to the development of novel barbituric acid derivatives with enhanced properties and diverse applications, with coverage of the literature relevant up to 2024.
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Open AccessArticle
New Generation of Hybrid Pyrazole–Tetrazole Tetrapodal Compounds: Synthesis and Biological Activities
by
Malika Amanchar, Tarik Harit, Mounir Cherfi, Meryem Idrissi Yahyaoui, Nour Elhouda Daoudi, Abderrahmane Yahyi, Abdeslam Asehraou and Fouad Malek
Organics 2024, 5(3), 290-297; https://doi.org/10.3390/org5030016 - 4 Sep 2024
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The elaboration of a new family of tetrapodal molecules L1–L3 bearing two pyrazole–tetrazole units is presented. The structure assigned to such molecules was verified by various techniques, including FTIR, NMR, HRMS and elemental analysis. The ability of these tetrapods to inhibit
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The elaboration of a new family of tetrapodal molecules L1–L3 bearing two pyrazole–tetrazole units is presented. The structure assigned to such molecules was verified by various techniques, including FTIR, NMR, HRMS and elemental analysis. The ability of these tetrapods to inhibit the growth of four fungal strains was examined, and the obtained results showed that they have some antifungal potency in the range of 12–16 mm. The alpha-amylase inhibition activity of these molecules was also evaluated. The obtained IC50 values (1.34 × 10−1–1.2 × 10−2 mg/mL) demonstrated that all compounds are potent enough to inhibit this enzyme much better than the positive control acarbose (2.6 × 10−1 mg/mL). A docking study on the porcine alpha-amylase was performed, and the results were in good correlation with the experimental results.
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Open AccessReview
The Use of Heterocyclic Azo Dyes on Different Textile Materials: A Review
by
Lucia Emanuele and Maurizio D’Auria
Organics 2024, 5(3), 277-289; https://doi.org/10.3390/org5030015 - 20 Aug 2024
Abstract
The art of dyeing textiles has a long history, as natural dyes have been used since prehistoric times. With the development of synthetic dyes in the 19th century, the focus shifted from natural to synthetic dyes due to their superior properties. Recently, however,
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The art of dyeing textiles has a long history, as natural dyes have been used since prehistoric times. With the development of synthetic dyes in the 19th century, the focus shifted from natural to synthetic dyes due to their superior properties. Recently, however, interest in natural dyes has increased again due to environmental and health concerns. Among industrial dyes, heterocyclic dyes, especially azo dyes, are of great importance due to their color brilliance and fastness. This review examines the synthesis, application, and analysis of azo dyes, especially heterocyclic dyes. It deals with monoazo, diazo, and polyazo dyes and highlights their structures, synthesis methods, and fastness properties. In addition, the ecological impact of azo dyes and practical solutions for their synthesis and application are discussed.
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(This article belongs to the Special Issue Chemistry of Heterocyclic Compounds)
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Open AccessArticle
Aromatic Functionalized Indanones and Indanols: Broad Spectrum Intermediates for Drug Candidate Diversification
by
Thomas C. Nugent and Nilesh N. Shitole
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).
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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.
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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.
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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.
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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.
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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 2
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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 [...]
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(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.
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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.
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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.
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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.
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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.
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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.
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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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Atoms, Crystals, Molecules, Organics, Symmetry, Inorganics
Advances in Molecular Symmetry and Chirality Research
Topic Editors: Ralph N. Salvatore, Guzman Gil-RamirezDeadline: 31 March 2026
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Special Issue in
Organics
Chemistry of Heterocyclic Compounds
Guest Editors: Lucia Emanuele, Maurizio D’AuriaDeadline: 31 October 2024
Special Issue in
Organics
Synthesis and Applications of Fluorescent Carbon Dots
Guest Editors: Patrícia D. Barata, Alexandra CostaDeadline: 30 November 2024
Special Issue in
Organics
Advanced and Green Synthetic Methodologies in Organic Chemistry
Guest Editor: Ioannis LykakisDeadline: 31 December 2024
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Organics
Advanced Research Papers in Organics
Collection Editors: Wim Dehaen, Michal Szostak, Huaping Xu