A new, simple, and efficient method for the synthesis of 3-aminohydantoins was reported in two steps, starting from the corresponding l-amino esters. Commercially available α-amino esters were converted into the corresponding isocyanate derivatives, which were then subjected to the condensation reaction with hydrazine hydrate and arylhydrazines, in the presence of DMAP and DIPEA. This method provides the corresponding 3-aminohydantoins in moderate and good yields under a simple and practical protocol.
{"title":"New Synthesis of 3-Aminohydantoins via Condensation of Hydrazines with Isocyanates Derived from α-Amino Esters","authors":"Houda Bouchnak, Thierry Ollevier, Jamil Kraïem","doi":"10.1055/a-2217-6821","DOIUrl":"https://doi.org/10.1055/a-2217-6821","url":null,"abstract":"<p>A new, simple, and efficient method for the synthesis of 3-aminohydantoins was reported in two steps, starting from the corresponding <i>\u0000<sc>l</sc>\u0000</i>-amino esters. Commercially available α-amino esters were converted into the corresponding isocyanate derivatives, which were then subjected to the condensation reaction with hydrazine hydrate and arylhydrazines, in the presence of DMAP and DIPEA. This method provides the corresponding 3-aminohydantoins in moderate and good yields under a simple and practical protocol.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"231 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138575964","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
We describe the use of biocompatible gum acacia (GA)-assembled Ag-TiO2 and Ag-SiO2 nanostructures as effective heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles through the traditional [3+2] cycloaddition of aryl nitriles with sodium azides. Characterization of the prepared catalysts employing TEM, XPS, FE-SEM, FT-IR, XRD, and TGA-DTG reveals silver nanoparticles encapsulated in the GA matrix amidst modified nano titania or silica. A variety of structurally divergent aryl nitriles were converted into the corresponding tetrazoles in a short reaction time. Other advantages include low catalytic load, easy handling of catalyst, limited use of toxic reagents, and desirable conversion yields, making this protocol a viable and practical alternative for this cyclization. The catalysts can be easily recovered and reused over multiple cycles without significant loss of catalytic activity.
{"title":"Gum Acacia Stabilized Ag-TiO2 and Ag-SiO2: Sustainable Nanocatalysts for Direct and Convenient Synthesis of 5-Substituted 1H-tetrazoles","authors":"Supriya Prakash, Bojja Sreedhar, N. V. S. Naidu","doi":"10.1055/s-0042-1751511","DOIUrl":"https://doi.org/10.1055/s-0042-1751511","url":null,"abstract":"<p>We describe the use of biocompatible gum acacia (GA)-assembled Ag-TiO<sub>2</sub> and Ag-SiO<sub>2</sub> nanostructures as effective heterogeneous catalysts for the synthesis of 5-substituted 1<i>H</i>-tetrazoles through the traditional [3+2] cycloaddition of aryl nitriles with sodium azides. Characterization of the prepared catalysts employing TEM, XPS, FE-SEM, FT-IR, XRD, and TGA-DTG reveals silver nanoparticles encapsulated in the GA matrix amidst modified nano titania or silica. A variety of structurally divergent aryl nitriles were converted into the corresponding tetrazoles in a short reaction time. Other advantages include low catalytic load, easy handling of catalyst, limited use of toxic reagents, and desirable conversion yields, making this protocol a viable and practical alternative for this cyclization. The catalysts can be easily recovered and reused over multiple cycles without significant loss of catalytic activity.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"14 2","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-11-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138524259","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract During the previous couple of decades, transition-metal (Fe, Co, Cu, Ni, Ru, Rh, Pd, Ag, Au) catalyzed inter- and intramolecular coupling reactions have attracted huge attention for the construction of C–C and C–heteroatom (like C–N, C–P, C–O, C–S, etc.) bonds to synthesize a diverse range of polymers, fine chemicals, and agrochemicals (mainly fungicides, herbicides, and insecticides), as well as biologically and pharmaceutically important organic molecules. Furthermore, the employment of lower cost and easily available metals such as first-row transition-metal salts or metal complexes of Fe, Co, Cu, Ni as catalysts compared to the precious metals such as Pd, Ag, Au in cross-coupling reactions have led to major advances in applications within the fields of synthesis. A number of cross-coupling reactions catalyzed by transition metals have been explored, including Suzuki, Heck, Sonogashira, Stille, Kumada, Kochi, Murahashi, Corriu, and Negishi reactions, as well as carbonylative, decarboxylative, reactions and α-arylations. In this review, we offer a comprehensive summary of the cross-coupling reaction catalyzed by different transition metals from the year 2009 to date. 1 Introduction 2 Pd-Catalyzed Reactions 2.1 C–C Cross-Coupling Reactions 2.2 C–N Cross-Coupling Reactions 2.3 C–P Cross-Coupling Reactions 3 Ni-Catalyzed Cross-Coupling Reactions 3.1 C–C Cross-Coupling Reactions 4 Cu-Catalyzed Cross-Coupling Reactions 4.1 C–C Cross-Coupling Reactions 4.2 C–O Cross-Coupling Reactions 4.2 C–N Cross-Coupling Reactions 4.4 C–P Cross-Coupling Reactions 4.5 C–Se Cross-Coupling Reactions 4.6 C–S Cross-Coupling Reactions 5 Fe-Catalyzed Reactions 5.1 C–C Cross-Coupling Reactions 5.2 C–S Cross-Coupling Reactions 6 Co-Catalyzed Reactions 7 Transition-Metal Nanoparticle-Promoted Reactions 7.1 Pd Nanoparticles 7.2 Cu Nanoparticles 8 Miscellaneous Reactions 9 Perspectives and Future Directions
{"title":"A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview","authors":"Anil Kumar, Saurav Kumar, Jyoti Jyoti, Deepak Gupta, Gajendra Singh","doi":"10.1055/s-0040-1720096","DOIUrl":"https://doi.org/10.1055/s-0040-1720096","url":null,"abstract":"Abstract During the previous couple of decades, transition-metal (Fe, Co, Cu, Ni, Ru, Rh, Pd, Ag, Au) catalyzed inter- and intramolecular coupling reactions have attracted huge attention for the construction of C–C and C–heteroatom (like C–N, C–P, C–O, C–S, etc.) bonds to synthesize a diverse range of polymers, fine chemicals, and agrochemicals (mainly fungicides, herbicides, and insecticides), as well as biologically and pharmaceutically important organic molecules. Furthermore, the employment of lower cost and easily available metals such as first-row transition-metal salts or metal complexes of Fe, Co, Cu, Ni as catalysts compared to the precious metals such as Pd, Ag, Au in cross-coupling reactions have led to major advances in applications within the fields of synthesis. A number of cross-coupling reactions catalyzed by transition metals have been explored, including Suzuki, Heck, Sonogashira, Stille, Kumada, Kochi, Murahashi, Corriu, and Negishi reactions, as well as carbonylative, decarboxylative, reactions and α-arylations. In this review, we offer a comprehensive summary of the cross-coupling reaction catalyzed by different transition metals from the year 2009 to date. 1 Introduction 2 Pd-Catalyzed Reactions 2.1 C–C Cross-Coupling Reactions 2.2 C–N Cross-Coupling Reactions 2.3 C–P Cross-Coupling Reactions 3 Ni-Catalyzed Cross-Coupling Reactions 3.1 C–C Cross-Coupling Reactions 4 Cu-Catalyzed Cross-Coupling Reactions 4.1 C–C Cross-Coupling Reactions 4.2 C–O Cross-Coupling Reactions 4.2 C–N Cross-Coupling Reactions 4.4 C–P Cross-Coupling Reactions 4.5 C–Se Cross-Coupling Reactions 4.6 C–S Cross-Coupling Reactions 5 Fe-Catalyzed Reactions 5.1 C–C Cross-Coupling Reactions 5.2 C–S Cross-Coupling Reactions 6 Co-Catalyzed Reactions 7 Transition-Metal Nanoparticle-Promoted Reactions 7.1 Pd Nanoparticles 7.2 Cu Nanoparticles 8 Miscellaneous Reactions 9 Perspectives and Future Directions","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"78 3","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135715619","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Simranpreet K Wahan, Pooja A Chawla, Parvesh Singh, Rupesh Kumar, Gaurav Bhargava
A highly eco-friendly greener approach based on the mechanochemical method using mortar and pestle is explored for the preparation of a variety of functionalized 4-thiazolidinones. The developed methodology does not require the use of harmful or expensive reagents and organic solvents and requires very less reaction time with easy isolation. The explored greener approach for the synthesis of 4-thiazolidinones is an important in terms of their usefulness for their valuable pharmacological properties.
{"title":"A FACILE, MECHANOCHEMICAL, SOLVENT AND CATALYST-FREE SYNTHESIS OF FUNCTIONALIZED 4-THIAZOLIDINONES","authors":"Simranpreet K Wahan, Pooja A Chawla, Parvesh Singh, Rupesh Kumar, Gaurav Bhargava","doi":"10.1055/a-2190-9678","DOIUrl":"https://doi.org/10.1055/a-2190-9678","url":null,"abstract":"A highly eco-friendly greener approach based on the mechanochemical method using mortar and pestle is explored for the preparation of a variety of functionalized 4-thiazolidinones. The developed methodology does not require the use of harmful or expensive reagents and organic solvents and requires very less reaction time with easy isolation. The explored greener approach for the synthesis of 4-thiazolidinones is an important in terms of their usefulness for their valuable pharmacological properties.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"55 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135968628","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The Gewald reaction has been well-known for more than half a century as an excellent method providing bioactive 2-aminothiophene heterocycles from the reaction of carbonyl compounds, α cyanoacetates, and elemental sulfur, in the presence of amines in stoichiometric amounts. This work describes the use of salts of boric acid as conjugate acid-base pair in a truly catalytic amount for the cyclocondensation of ketones with active methylenes like malononitrile, ethyl cyanoacetate, and benzoyl acetonitrile with sulfur to give 2-aminothiophenes via Gewald reaction. The present protocol is also applied for synthesizing Tinoridine an anti-peroxidative NSAID with an excellent yield. Additionally, the catalyst has great recyclability and reusability.
{"title":"Truly catalytic Gewald synthesis of 2-aminothiophenes using piperidinium borate (Pip borate), a conjugate acid-base pair","authors":"Kanchan Gavali, Ganesh U Chaturbhuj","doi":"10.1055/a-2189-3334","DOIUrl":"https://doi.org/10.1055/a-2189-3334","url":null,"abstract":"The Gewald reaction has been well-known for more than half a century as an excellent method providing bioactive 2-aminothiophene heterocycles from the reaction of carbonyl compounds, α cyanoacetates, and elemental sulfur, in the presence of amines in stoichiometric amounts. This work describes the use of salts of boric acid as conjugate acid-base pair in a truly catalytic amount for the cyclocondensation of ketones with active methylenes like malononitrile, ethyl cyanoacetate, and benzoyl acetonitrile with sulfur to give 2-aminothiophenes via Gewald reaction. The present protocol is also applied for synthesizing Tinoridine an anti-peroxidative NSAID with an excellent yield. Additionally, the catalyst has great recyclability and reusability.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"215 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136292358","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ram Sagar, Uma Shankar, Ashish Khanna, Kavita Singh, Ghanshyam Tiwari
Lawsone, also known as 2-hydroxy-1,4-naphthoquinone, has been extensively studied and found to be a crucial precursor in the production of a diverse range of natural products like molecular scaffolds, which are highly sought after for biological research purposes. Due to its unique chemical composition, Lawsone has been utilized for over a century as a starting material for the synthesis of numerous biologically active molecules and materials, showcasing intriguing properties across a wide range of scientific and technological applications. Additionally, Lawsone has been widely used in organic synthesis processes, with its various applications. The recent advances in the synthesis of different scaffolds starting from Lawsone and their applications are being discussed in details in the current review covering the literature during the period of 2017-2023.
{"title":"Recent advances in the synthetic developments on the 2-hydroxy-1,4-naphthoquinone (Lawsone)","authors":"Ram Sagar, Uma Shankar, Ashish Khanna, Kavita Singh, Ghanshyam Tiwari","doi":"10.1055/a-2187-3835","DOIUrl":"https://doi.org/10.1055/a-2187-3835","url":null,"abstract":"Lawsone, also known as 2-hydroxy-1,4-naphthoquinone, has been extensively studied and found to be a crucial precursor in the production of a diverse range of natural products like molecular scaffolds, which are highly sought after for biological research purposes. Due to its unique chemical composition, Lawsone has been utilized for over a century as a starting material for the synthesis of numerous biologically active molecules and materials, showcasing intriguing properties across a wide range of scientific and technological applications. Additionally, Lawsone has been widely used in organic synthesis processes, with its various applications. The recent advances in the synthesis of different scaffolds starting from Lawsone and their applications are being discussed in details in the current review covering the literature during the period of 2017-2023.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"10 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135346293","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Electrochemical synthesis has become an appealing and powerful substitute for traditional methods for oxidizing and reducing organic compounds, due to its environmentally benign, sustainable, and practical nature. Thus, numerous valuable changes have been established in the field of organic synthesis through the utilization of electrochemistry. Among these electrochemical transformations, the C–Se bond formation stands out as an exceptionally noteworthy reaction type. In this graphical review, we present a succinct summary of the progress in utilizing electrochemical strategies for synthesizing organoselenium compounds.
{"title":"Electrochemical Synthesis of Organoselenium Compounds：A Graphical Review","authors":"Balati Hasimujiang, Zhixiong Ruan","doi":"10.1055/a-2184-8411","DOIUrl":"https://doi.org/10.1055/a-2184-8411","url":null,"abstract":"Electrochemical synthesis has become an appealing and powerful substitute for traditional methods for oxidizing and reducing organic compounds, due to its environmentally benign, sustainable, and practical nature. Thus, numerous valuable changes have been established in the field of organic synthesis through the utilization of electrochemistry. Among these electrochemical transformations, the C–Se bond formation stands out as an exceptionally noteworthy reaction type. In this graphical review, we present a succinct summary of the progress in utilizing electrochemical strategies for synthesizing organoselenium compounds.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"53 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135792650","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract This article describes the use of N-bromosuccinimide in different organic group transformations in carbohydrate chemistry. A comprehensive discussion on the synthesis of deoxysugars through selective O-benzylidene fragmentation, photobromination, halogenation, oxidation, and polymerisation of different carbohydrate moieties with the aid of N-bromosuccinimide (NBS) is presented. The use of NBS in the most significant glycosylation methods and in oligosaccharide synthesis is also discussed.
{"title":"Application of N-Bromosuccinimide in Carbohydrate Chemistry","authors":"Smritilekha Bera, Dhananjoy Mondal, Bhaskar Chatterjee","doi":"10.1055/s-0042-1751501","DOIUrl":"https://doi.org/10.1055/s-0042-1751501","url":null,"abstract":"Abstract This article describes the use of N-bromosuccinimide in different organic group transformations in carbohydrate chemistry. A comprehensive discussion on the synthesis of deoxysugars through selective O-benzylidene fragmentation, photobromination, halogenation, oxidation, and polymerisation of different carbohydrate moieties with the aid of N-bromosuccinimide (NBS) is presented. The use of NBS in the most significant glycosylation methods and in oligosaccharide synthesis is also discussed.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"193 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135964037","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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