Pub Date : 2024-05-13DOI: 10.2174/0113852728303168240424052507
Tanushree Sen, Suman Adhikari, Nabajyoti Baildya, Kumaresh Ghosh
: Three receptors 1-3, built on adenine, have been synthesized, structurally characterized, and successfully employed for the recognition of monocarboxylic acids. The adenine-based receptors 1-3 have been found to bind monocarboxylic acids via the Hoogsteen (HG) binding site or the Watson-Crick (WC) binding site and form 1:1 complexes in CHCl3. Detailed binding of the receptors 1-3, in the presence of the monocarboxylic acids, corroborates that there is a distinct propensity of the HG site for aromatic carboxylic acids, for example, (S)-mandelic acid and benzoic acid. Aliphatic acids, for example, propanoic acid and rac-lactic acid, on the other hand, prefer to bind at the WC site. The monocarboxylic acid bindings to 1-3 were examined by UV–Vis, fluorescence, and 1 H NMR spectroscopic methods, and DFT study.
{"title":"Functionalized Adenine-Based Receptors for Monocarboxylic Acids’ Recognition","authors":"Tanushree Sen, Suman Adhikari, Nabajyoti Baildya, Kumaresh Ghosh","doi":"10.2174/0113852728303168240424052507","DOIUrl":"https://doi.org/10.2174/0113852728303168240424052507","url":null,"abstract":": Three receptors 1-3, built on adenine, have been synthesized, structurally characterized, and successfully employed for the recognition of monocarboxylic acids. The adenine-based receptors 1-3 have been found to bind monocarboxylic acids via the Hoogsteen (HG) binding site or the Watson-Crick (WC) binding site and form 1:1 complexes in CHCl3. Detailed binding of the receptors 1-3, in the presence of the monocarboxylic acids, corroborates that there is a distinct propensity of the HG site for aromatic carboxylic acids, for example, (S)-mandelic acid and benzoic acid. Aliphatic acids, for example, propanoic acid and rac-lactic acid, on the other hand, prefer to bind at the WC site. The monocarboxylic acid bindings to 1-3 were examined by UV–Vis, fluorescence, and 1 H NMR spectroscopic methods, and DFT study.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140937494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-13DOI: 10.2174/0113852728248318240418092208
Sayed K. Ramadan, Sameh A. Rizk, Eman A.E. El-Helw
: This survey provides information on the synthesis and biological applications of coumarinylchalcones. Chalcones are unsaturated ketones involving the reactive keto-ethylenic group (CO-CH=CH). Chalcones are naturally abundant in many medical plants, including vegetables, fruits, and foods. Natural and synthetic chalcone compounds exhibit a broad spectrum of biological properties like anticancer, antiinflammatory, anti-HIV, antioxidant, antimalarial, and antimicrobial. Some conventional, microwave, and grinding techniques have been utilized for the synthesis of chalcones. Noteworthy, the Claisen-Schmidt condensation reaction remains the most popular and effective method for synthesis. It summarizes information about its synthetic methods as building blocks in some reactions like cyclization reactions and medical applications. This review article presents an overview of approaches and biological data for chalcones bearing a coumarin scaffold.
{"title":"Synthesis and Biological Applications of Coumarinyl-Chalcones","authors":"Sayed K. Ramadan, Sameh A. Rizk, Eman A.E. El-Helw","doi":"10.2174/0113852728248318240418092208","DOIUrl":"https://doi.org/10.2174/0113852728248318240418092208","url":null,"abstract":": This survey provides information on the synthesis and biological applications of coumarinylchalcones. Chalcones are unsaturated ketones involving the reactive keto-ethylenic group (CO-CH=CH). Chalcones are naturally abundant in many medical plants, including vegetables, fruits, and foods. Natural and synthetic chalcone compounds exhibit a broad spectrum of biological properties like anticancer, antiinflammatory, anti-HIV, antioxidant, antimalarial, and antimicrobial. Some conventional, microwave, and grinding techniques have been utilized for the synthesis of chalcones. Noteworthy, the Claisen-Schmidt condensation reaction remains the most popular and effective method for synthesis. It summarizes information about its synthetic methods as building blocks in some reactions like cyclization reactions and medical applications. This review article presents an overview of approaches and biological data for chalcones bearing a coumarin scaffold.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140937370","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-09DOI: 10.2174/0113852728297985240408062346
Zahra Movahed, Hassan Valizadeh, Farzaneh Mirzaei
: Polysubstituted pyridine derivatives were producedwith high to excellent yields in the presence of nitrogen-doped graphene (NDG) as a dual acid–based catalyst. NDG efficiently catalyzes the multicomponent reaction between arylaldehydes, diethyl-acetylene dicarboxylates, malononitrile, and ammonium acetate under solvent-free conditions at 80°C to afford the polysubstituted pyridines in short reaction times. The structures of the synthesized pyridines were established by Ft-IR, 1H, and 13C NMR spectroscopic analysis. The advantages of this method include the in-situ oxidation of prepared 1,4-dihydropyridines, one-pot procedure, solventless system, operational simplicity, and no column chromatography. Additionally, neither toxic solvents nor catalysts are needed, and the procedure can be very reliable among the reported methodologies. The yields and reaction times in the presence of four times recycled catalyst are in comparable to the fresh catalyst. background: Graphene quantum dots have attracted considerable attention of chemists because of their unique properties such as: stability, non-toxicity, good water solubility, biocompatibility. In continuation of our interest in using ionic liquids, water or solvent-free systems as green reaction media in organic reactions for the synthesis of important compounds , we wish to report here efficient synthesis of polysubstituted pyridine derivatives in high to excellent yields using Nitrogen-doped graphene as efficient catalyst.
{"title":"Synthesis of Polysubstituted Pyridines via Nitrogen-doped Graphene Catalyzed One-Pot Multicomponent Reaction under Solvent-Free Conditions","authors":"Zahra Movahed, Hassan Valizadeh, Farzaneh Mirzaei","doi":"10.2174/0113852728297985240408062346","DOIUrl":"https://doi.org/10.2174/0113852728297985240408062346","url":null,"abstract":": Polysubstituted pyridine derivatives were producedwith high to excellent yields in the presence of nitrogen-doped graphene (NDG) as a dual acid–based catalyst. NDG efficiently catalyzes the multicomponent reaction between arylaldehydes, diethyl-acetylene dicarboxylates, malononitrile, and ammonium acetate under solvent-free conditions at 80°C to afford the polysubstituted pyridines in short reaction times. The structures of the synthesized pyridines were established by Ft-IR, 1H, and 13C NMR spectroscopic analysis. The advantages of this method include the in-situ oxidation of prepared 1,4-dihydropyridines, one-pot procedure, solventless system, operational simplicity, and no column chromatography. Additionally, neither toxic solvents nor catalysts are needed, and the procedure can be very reliable among the reported methodologies. The yields and reaction times in the presence of four times recycled catalyst are in comparable to the fresh catalyst. background: Graphene quantum dots have attracted considerable attention of chemists because of their unique properties such as: stability, non-toxicity, good water solubility, biocompatibility. In continuation of our interest in using ionic liquids, water or solvent-free systems as green reaction media in organic reactions for the synthesis of important compounds , we wish to report here efficient synthesis of polysubstituted pyridine derivatives in high to excellent yields using Nitrogen-doped graphene as efficient catalyst.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"43 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140937423","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-06DOI: 10.2174/0113852728306541240409034052
Shan Jiang, Miao Wang
: Recently, the concept of mechanoredox chemistry has been proposed and well-developed in organic synthesis. Mechanoredox chemistry is conceptually similar to a photocatalyst reaction system, where piezoelectric materials are introduced to the reaction system in a manner analogous to photoredox catalysis. These reactions feature the ability to generate high-value radicals that do not require harsh reaction conditions of anhydrous and anaerobic conditions, an expensive photocatalyst, and the use of solvents, which renders these transformations highly industrially applicable. In addition, mechanoredox chemistry is also an emerging interdisciplinary research field that combines material chemistry with synthetic chemistry to create more useful reactions. This review provides a comprehensive summary of progress to date in the specific transformation and related mechanisms of piezoelectric-mediated mechanoredox reactions by ball milling in organic synthesis.
{"title":"A Review on Piezoelectric-Mediated Mechanoredox Reactions by Ball Milling in Organic Synthesis","authors":"Shan Jiang, Miao Wang","doi":"10.2174/0113852728306541240409034052","DOIUrl":"https://doi.org/10.2174/0113852728306541240409034052","url":null,"abstract":": Recently, the concept of mechanoredox chemistry has been proposed and well-developed in organic synthesis. Mechanoredox chemistry is conceptually similar to a photocatalyst reaction system, where piezoelectric materials are introduced to the reaction system in a manner analogous to photoredox catalysis. These reactions feature the ability to generate high-value radicals that do not require harsh reaction conditions of anhydrous and anaerobic conditions, an expensive photocatalyst, and the use of solvents, which renders these transformations highly industrially applicable. In addition, mechanoredox chemistry is also an emerging interdisciplinary research field that combines material chemistry with synthetic chemistry to create more useful reactions. This review provides a comprehensive summary of progress to date in the specific transformation and related mechanisms of piezoelectric-mediated mechanoredox reactions by ball milling in organic synthesis.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"43 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884953","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Azepine is a privileged nitrogen-containing ring that has been found to display a wide range of biological activities. Azepine is a valuable skeleton in designing novel compounds in medicinal chemistry due to its interesting chemical and biological properties. The study on the synthesis of this ring system engenders a fascinating area of research owing to its potential to form an active pharmacophore for De Novo exploration. In this study, conventional and domino results were compared to access the diverse set of azepines in high yield. The domino approach has revolutionized the way through which the previously impossible yet significant transformations could be conceptualized, allowing the construction of difficult materials in one step. The aim of the present mini-review is to highlight the importance of the one-pot domino reaction for the synthesis of condensed azepines. This review also presents research on this subject from the past two decades.
{"title":"One-Pot Synthesis of Condensed Azepines","authors":"Khushboo Bhardwaj, Shivangi Jaiswal, Annu Bhardwaj, Dharma Kishore, Jaya Dwivedi, Swapnil Sharma","doi":"10.2174/0113852728300551240408054904","DOIUrl":"https://doi.org/10.2174/0113852728300551240408054904","url":null,"abstract":": Azepine is a privileged nitrogen-containing ring that has been found to display a wide range of biological activities. Azepine is a valuable skeleton in designing novel compounds in medicinal chemistry due to its interesting chemical and biological properties. The study on the synthesis of this ring system engenders a fascinating area of research owing to its potential to form an active pharmacophore for De Novo exploration. In this study, conventional and domino results were compared to access the diverse set of azepines in high yield. The domino approach has revolutionized the way through which the previously impossible yet significant transformations could be conceptualized, allowing the construction of difficult materials in one step. The aim of the present mini-review is to highlight the importance of the one-pot domino reaction for the synthesis of condensed azepines. This review also presents research on this subject from the past two decades.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"147 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884871","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-06DOI: 10.2174/0113852728304619240408045311
Marcio C. S. de Mattos
: Trihaloisocyanuric acids [1,3,5-trihalo-1,3,5-triazine-2,4,6-(1H,3H,5H)-triones] are commercially available or easily prepared solids. They are highly reactive, stable, easily handled, and have an excellent atom economy, transferring up to three halogen atoms to organic substrates. In these regards, the present review summarizes their synthetic applications as safe and convenient reagents. Therefore, electrophilic halogenation reactions of alkenes, alkynes, arenes, heteroarenes, carbonyl compounds, and heteroatoms, as well as radical halogenation involving saturated substrates and in situ halogenated intermediates for Appel-type reactions are presented and discussed. Remarkably, applications of trihaloisocyanuric acids in processes for the construction of heteroarene scaffolds based on electrophilic halo- and oxidative cyclization, multicomponent reactions, and telescopic reactions are also given.
{"title":"Trihaloisocyanuric Acids: Useful Reagents for Halogenation Reactions and Heterocyclic Scaffold Construction","authors":"Marcio C. S. de Mattos","doi":"10.2174/0113852728304619240408045311","DOIUrl":"https://doi.org/10.2174/0113852728304619240408045311","url":null,"abstract":": Trihaloisocyanuric acids [1,3,5-trihalo-1,3,5-triazine-2,4,6-(1H,3H,5H)-triones] are commercially available or easily prepared solids. They are highly reactive, stable, easily handled, and have an excellent atom economy, transferring up to three halogen atoms to organic substrates. In these regards, the present review summarizes their synthetic applications as safe and convenient reagents. Therefore, electrophilic halogenation reactions of alkenes, alkynes, arenes, heteroarenes, carbonyl compounds, and heteroatoms, as well as radical halogenation involving saturated substrates and in situ halogenated intermediates for Appel-type reactions are presented and discussed. Remarkably, applications of trihaloisocyanuric acids in processes for the construction of heteroarene scaffolds based on electrophilic halo- and oxidative cyclization, multicomponent reactions, and telescopic reactions are also given.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"50 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884951","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-06DOI: 10.2174/0113852728304549240328064426
Radell Echemendía, Kauê C. Capellaro, Antonio C. B. Burtoloso
: Photochemical reactions offer unparalleled opportunities to access elusive chemical pathways and develop innovative strategies for constructing complex molecules. Within organic synthesis, photochemical reactions have become indispensable tools for accessing complex molecular structures, such as pharmaceuticals and natural products. The ability of sulfur ylides to participate in these diverse processes has made them indispensable tools in the synthetic chemist's toolbox. The use of sulfur ylides in photochemical transformations has garnered significant attention in the synthetic organic chemistry community, and they serve as powerful intermediates in several chemical transformations. This review article presents a comprehensive overview of the photochemical reactions mediated by sulfur ylides. Herein, we describe the key aspects of the reactivity of sulfur ylides in the presence of light. The reactivity of these compounds can be classified into three categories: sulfur ylides as energy acceptors, as electron donors, and as trapping reagents.
{"title":"Photochemical Reactions of Sulfur Ylides#","authors":"Radell Echemendía, Kauê C. Capellaro, Antonio C. B. Burtoloso","doi":"10.2174/0113852728304549240328064426","DOIUrl":"https://doi.org/10.2174/0113852728304549240328064426","url":null,"abstract":": Photochemical reactions offer unparalleled opportunities to access elusive chemical pathways and develop innovative strategies for constructing complex molecules. Within organic synthesis, photochemical reactions have become indispensable tools for accessing complex molecular structures, such as pharmaceuticals and natural products. The ability of sulfur ylides to participate in these diverse processes has made them indispensable tools in the synthetic chemist's toolbox. The use of sulfur ylides in photochemical transformations has garnered significant attention in the synthetic organic chemistry community, and they serve as powerful intermediates in several chemical transformations. This review article presents a comprehensive overview of the photochemical reactions mediated by sulfur ylides. Herein, we describe the key aspects of the reactivity of sulfur ylides in the presence of light. The reactivity of these compounds can be classified into three categories: sulfur ylides as energy acceptors, as electron donors, and as trapping reagents.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884874","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-03DOI: 10.2174/0113852728239522231006064747
Stanisław Ostrowski, Sebastian Grzyb, Bartosz Godlewski
:: The synthesis of meso-tetraphenylporphyrin derivatives, double functionalized in one of the phenyl rings (with a nitro group and carbon substituents), is described. 5-(4- Nitroaryl)-10,15,20-triarylporphyrinates react, in the presence of a base (t-BuOK), with carbanions containing a leaving group at the carbanionic center to give products of substitution of hydrogen at ortho-position to the nitro group via vicarious nucleophilic substitution scheme. Their alkylation with allyl bromide or 4-bromobut-1-en (t-BuOK/DMF, at 0-5°C) leads to porphyrins bearing side alkyl chain with a terminal double bond in yields of up to 82%. The double-substituted intermediates are very convenient substrates for Heck cross-coupling reactions. In this study, the synthesis of porphyrin–azulene dyads is reported. In some cases, the formation of highly conjugated systems is observed, with moderate yield. Their structures are interesting from both the porphyrin and azulene point of view.
{"title":"Some Terminally Alkenyl-substituted Porphyrins: Synthesis and Attempts of Heck Reaction Leading to Porphyrin-Azulene Dyads","authors":"Stanisław Ostrowski, Sebastian Grzyb, Bartosz Godlewski","doi":"10.2174/0113852728239522231006064747","DOIUrl":"https://doi.org/10.2174/0113852728239522231006064747","url":null,"abstract":":: The synthesis of meso-tetraphenylporphyrin derivatives, double functionalized in one of the phenyl rings (with a nitro group and carbon substituents), is described. 5-(4- Nitroaryl)-10,15,20-triarylporphyrinates react, in the presence of a base (t-BuOK), with carbanions containing a leaving group at the carbanionic center to give products of substitution of hydrogen at ortho-position to the nitro group via vicarious nucleophilic substitution scheme. Their alkylation with allyl bromide or 4-bromobut-1-en (t-BuOK/DMF, at 0-5°C) leads to porphyrins bearing side alkyl chain with a terminal double bond in yields of up to 82%. The double-substituted intermediates are very convenient substrates for Heck cross-coupling reactions. In this study, the synthesis of porphyrin–azulene dyads is reported. In some cases, the formation of highly conjugated systems is observed, with moderate yield. Their structures are interesting from both the porphyrin and azulene point of view.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140840104","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-03DOI: 10.2174/0113852728299375240405053207
Silvia E. Loredo-Carrillo, Elisa Leyva, Lluvia Itzel López-López, Gabriela Navarro-Tovar, Denisse de Loera, Sarai Vega-Rodríguez
: An alternative to finding new drugs for the treatment of various diseases is the chemical modification of the structure of compounds of natural origin. Among them, naphthoquinones are very interesting candidates, as they are antibacterial, antifungal, antiparasitic, and anticancer agents. Naphthoquinones are redox compounds that can accept one or two electrons, generating reactive oxygen species in the cell and producing cell apoptosis. Naphthoquinones are unsaturated compounds containing a dicarbonyl sequence in the para position, which is highly reactive. Several studies of the chemical modification of naphthoquinones, either of natural origin (such as lapachol or juglone) or synthetic origin, have demonstrated the great importance and versatility of this type of compound. Polyhydroxylated derivatives, amino, thioethers, and conjugated heterosystems (indole or pyrrole groups) have been synthesized. Depending on the type of derivative, their specific use against certain types of microorganisms or cancer cell lines has been demonstrated.
{"title":"Description of Some Methodologies for the Synthesis of 1,4-Naphthoquinone Derivatives and Examples of their Biological Activity: A Review","authors":"Silvia E. Loredo-Carrillo, Elisa Leyva, Lluvia Itzel López-López, Gabriela Navarro-Tovar, Denisse de Loera, Sarai Vega-Rodríguez","doi":"10.2174/0113852728299375240405053207","DOIUrl":"https://doi.org/10.2174/0113852728299375240405053207","url":null,"abstract":": An alternative to finding new drugs for the treatment of various diseases is the chemical modification of the structure of compounds of natural origin. Among them, naphthoquinones are very interesting candidates, as they are antibacterial, antifungal, antiparasitic, and anticancer agents. Naphthoquinones are redox compounds that can accept one or two electrons, generating reactive oxygen species in the cell and producing cell apoptosis. Naphthoquinones are unsaturated compounds containing a dicarbonyl sequence in the para position, which is highly reactive. Several studies of the chemical modification of naphthoquinones, either of natural origin (such as lapachol or juglone) or synthetic origin, have demonstrated the great importance and versatility of this type of compound. Polyhydroxylated derivatives, amino, thioethers, and conjugated heterosystems (indole or pyrrole groups) have been synthesized. Depending on the type of derivative, their specific use against certain types of microorganisms or cancer cell lines has been demonstrated.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140840113","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-02DOI: 10.2174/0113852728304402240403052919
Claudio J.A. Mota
: This mini-review reports the current routes used for the production of dimethyl carbonate (DMC), a green and versatile methylating reactant widely used in organic synthesis. The use of DMC in methylation processes is also discussed. The main routes of DMC production, encompassing the reaction between phosgene and methanol and the oxidative carbonylation of methanol with CO and urea methanolysis, are summarised. However, none of them can be considered entirely green, and the drawbacks in terms of green chemistry principles are addressed. The present commercial route to DMC, which involves the initial reaction of CO2 with ethylene oxide to produce ethylene carbonate that further reacts with excess methanol, is also explored regarding the green chemistry principles. Moreover, this review focuses on the direct DMC production from the reaction of methanol and CO2, discussing catalysts and strategies to shift equilibrium. An emphasis is given to heterogeneous catalysts, especially those based on CeO2. A final remark on the production of DMC through the capture of CO2 using chitosan-derived adsorbents and renewable methanol is addressed.
{"title":"Green Routes to Dimethyl Carbonate: A Green and Versatile Methylating Reactant","authors":"Claudio J.A. Mota","doi":"10.2174/0113852728304402240403052919","DOIUrl":"https://doi.org/10.2174/0113852728304402240403052919","url":null,"abstract":": This mini-review reports the current routes used for the production of dimethyl carbonate (DMC), a green and versatile methylating reactant widely used in organic synthesis. The use of DMC in methylation processes is also discussed. The main routes of DMC production, encompassing the reaction between phosgene and methanol and the oxidative carbonylation of methanol with CO and urea methanolysis, are summarised. However, none of them can be considered entirely green, and the drawbacks in terms of green chemistry principles are addressed. The present commercial route to DMC, which involves the initial reaction of CO2 with ethylene oxide to produce ethylene carbonate that further reacts with excess methanol, is also explored regarding the green chemistry principles. Moreover, this review focuses on the direct DMC production from the reaction of methanol and CO2, discussing catalysts and strategies to shift equilibrium. An emphasis is given to heterogeneous catalysts, especially those based on CeO2. A final remark on the production of DMC through the capture of CO2 using chitosan-derived adsorbents and renewable methanol is addressed.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140840353","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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