Abstract An efficient electrochemical oxidative C(sp2)–H sulfonylation of aldehyde hydrazones is described. A variety of sodium sufinates or sulfinic acids participate effectively in this protocol, which provides facile access to an array of alkyl and aromatic sulfonylated hydrazones with up to 96% yield. Large-scale synthesis and product derivatization show the potential utility of this methodology. Preliminary mechanistic investigations including radical-inhibition, electricity on/off experiments, and cyclic voltammetry support a radical pathway.
{"title":"Oxidative C–H Sulfonylation of Hydrazones Enabled by Electrochemistry","authors":"Qi-Liang Yang, Ping-Ping Lei, Hai-Ming Guo, Er-Jun Hao, Bei-Ning Zhang, Hong-Hao Zhou, Wan-Wan Li","doi":"10.1055/s-0042-1751510","DOIUrl":"https://doi.org/10.1055/s-0042-1751510","url":null,"abstract":"Abstract An efficient electrochemical oxidative C(sp2)–H sulfonylation of aldehyde hydrazones is described. A variety of sodium sufinates or sulfinic acids participate effectively in this protocol, which provides facile access to an array of alkyl and aromatic sulfonylated hydrazones with up to 96% yield. Large-scale synthesis and product derivatization show the potential utility of this methodology. Preliminary mechanistic investigations including radical-inhibition, electricity on/off experiments, and cyclic voltammetry support a radical pathway.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"207 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":"136093436","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}
Pooja A. Chawla, Simranpreet K. Wahan, Gaurav Bhargava
Abstract
摘要
{"title":"Chlorophyll: A Greener Catalyst in Synthetic Transformations","authors":"Pooja A. Chawla, Simranpreet K. Wahan, Gaurav Bhargava","doi":"10.1055/s-0042-1751515","DOIUrl":"https://doi.org/10.1055/s-0042-1751515","url":null,"abstract":"Abstract","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"209 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":"136128166","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}
Li Li, Guo-Liang Dai, Xue Hua Zhu, Lei Yu, Hai Yan Li
Abstract N,N′-Bis(3-pyridyl)methanediamine was prepared by treating 3-aminopyridine with formaldehyde in acetonitrile. By treating it with formaldehyde, the eight-membered heterocyclic ring compound 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane was prepared. This could occur in a two-step manner in a [3+1+3+1] cycloaddition reaction. The compounds were characterized by X-ray crystallography, 1H and 13C NMR spectroscopy, and mass spectrometry. The powder XRD pattern of 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane was also determined and revealed an uncommon twist-crown conformation, which was further confirmed by DFT calculations.
{"title":"Synthesis and Characterization of an Eight-Membered Heterocyclic 1,3,5,7-Tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane","authors":"Li Li, Guo-Liang Dai, Xue Hua Zhu, Lei Yu, Hai Yan Li","doi":"10.1055/s-0042-1751494","DOIUrl":"https://doi.org/10.1055/s-0042-1751494","url":null,"abstract":"Abstract N,N′-Bis(3-pyridyl)methanediamine was prepared by treating 3-aminopyridine with formaldehyde in acetonitrile. By treating it with formaldehyde, the eight-membered heterocyclic ring compound 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane was prepared. This could occur in a two-step manner in a [3+1+3+1] cycloaddition reaction. The compounds were characterized by X-ray crystallography, 1H and 13C NMR spectroscopy, and mass spectrometry. The powder XRD pattern of 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane was also determined and revealed an uncommon twist-crown conformation, which was further confirmed by DFT calculations.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"21 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":"135810726","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}
Ravi Varala, Narsimhaswamy Dubasi, Vittal Seema, Vijay Kotra
NaIO4 has been effectively investigated as a flexible oxidant for a range of fundamental chemical transformations, including the synthesis of bioactive natural compounds and intriguing oxidative transformations including C–H activation and oxidative functionalization of alkenes.
{"title":"Sodium Periodate (NaIO4) in Organic Synthesis","authors":"Ravi Varala, Narsimhaswamy Dubasi, Vittal Seema, Vijay Kotra","doi":"10.1055/a-2183-3678","DOIUrl":"https://doi.org/10.1055/a-2183-3678","url":null,"abstract":"NaIO4 has been effectively investigated as a flexible oxidant for a range of fundamental chemical transformations, including the synthesis of bioactive natural compounds and intriguing oxidative transformations including C–H activation and oxidative functionalization of alkenes.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"10 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135345255","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}
Deeksha Mudgal, Ravi Pratap Singh, Nisha Yadav, Vivek Mishra
Abstract A highly efficient catalyst, Cu-doped poly(N-[3-(dimethylamino)propyl]methacrylamide, acrylic acid, N-vinyl imidazole) (PDAI) magnetic carbon aerogel (CPIMCA), was successfully employed for the synthesis of isatin nitrone derivatives. The 3D porous CPIMCA catalyst demonstrated outstanding performance through the application of a coupling reaction between isatin oxime and phenylboronic acid derivatives, providing up to 98% yield of the required nitrone derivatives. Remarkably, the incorporation of copper within the polymeric structure of the magnetic carbon aerogel exhibited a significant influence on catalytic activity, even at a low overall copper content of approximately 2%. This was confirmed through EDX elemental mapping analysis, further establishing the competence of the catalyst for catalytic reactions. Comparative studies revealed that CPIMCA outperformed Cu(Oac)2 catalyst, providing a notable 10–15% increase in product yield. This superior performance can be attributed to the unique synergistic effect of copper, iron, and carbon aerogel as the polymeric matrix, highlighting the exceptional capabilities of CPIMCA as a catalyst.
{"title":"Exploring the catalytic efficiency of copper-doped Magnetic Carbon Aerogel towards the coupling reaction of Isatin Oxime with Phenylboronic Acid derivatives","authors":"Deeksha Mudgal, Ravi Pratap Singh, Nisha Yadav, Vivek Mishra","doi":"10.1055/a-2182-7757","DOIUrl":"https://doi.org/10.1055/a-2182-7757","url":null,"abstract":"Abstract A highly efficient catalyst, Cu-doped poly(N-[3-(dimethylamino)propyl]methacrylamide, acrylic acid, N-vinyl imidazole) (PDAI) magnetic carbon aerogel (CPIMCA), was successfully employed for the synthesis of isatin nitrone derivatives. The 3D porous CPIMCA catalyst demonstrated outstanding performance through the application of a coupling reaction between isatin oxime and phenylboronic acid derivatives, providing up to 98% yield of the required nitrone derivatives. Remarkably, the incorporation of copper within the polymeric structure of the magnetic carbon aerogel exhibited a significant influence on catalytic activity, even at a low overall copper content of approximately 2%. This was confirmed through EDX elemental mapping analysis, further establishing the competence of the catalyst for catalytic reactions. Comparative studies revealed that CPIMCA outperformed Cu(Oac)2 catalyst, providing a notable 10–15% increase in product yield. This superior performance can be attributed to the unique synergistic effect of copper, iron, and carbon aerogel as the polymeric matrix, highlighting the exceptional capabilities of CPIMCA as a catalyst.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"13 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135534606","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 A cost-effective, scalable, high-yielding, and commercially viable synthesis of 4-bromo-1,2-dimethyl-1H-imidazole (1), an important building block to construct various bioactive molecules has been established. The main feature of this method includes the selection of appropriate starting material 1,2-dimethyl-1H-imidazole in which the existing issue of regioisomer formation is circumvented and the selective debromination is accomplished by using isopropyl magnesium chloride.
{"title":"Cost-effective and scalable synthesis of 4-bromo-1,2-dimethyl-1H-imidazole: a key building block for numerous bioactive molecules","authors":"Vetrichelvan Muthalagu, Lanke Veeranjaneyulu, Bellam Chandu, Arvind Mathur, Anuradha Gupta","doi":"10.1055/a-2176-1585","DOIUrl":"https://doi.org/10.1055/a-2176-1585","url":null,"abstract":"Abstract A cost-effective, scalable, high-yielding, and commercially viable synthesis of 4-bromo-1,2-dimethyl-1H-imidazole (1), an important building block to construct various bioactive molecules has been established. The main feature of this method includes the selection of appropriate starting material 1,2-dimethyl-1H-imidazole in which the existing issue of regioisomer formation is circumvented and the selective debromination is accomplished by using isopropyl magnesium chloride.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"16 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135551946","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 A direct electrochemical amidation of xanthene was readily achieved under direct anodic oxidation. The reactivity of benzamides was significantly enhanced by the virtue of the solvent effect of hexafluoroisopropanol (HFIP). An obvious hydrogen bonding between HFIP and benzamide was detected, and the proton-coupled electron-transfer (PCET) effect was proposed for the enhancement effect of HFIP. In this transformation, a broad range of primary and secondary amides were readily used as amidating reagents, including l-proline-, naproxen-, and probencid-derived amides. We proposed a plausible reaction mechanism for this direct amidation based on the experimental observations.
{"title":"Direct Electrochemical C(sp3)-H Amidation Enabled by Hexafluoroisopropanol (HFIP)","authors":"Fengyi Li, Ke Liu, Qi Sun, Sheng Zhang, Man-Bo Li","doi":"10.1055/a-2176-1840","DOIUrl":"https://doi.org/10.1055/a-2176-1840","url":null,"abstract":"Abstract A direct electrochemical amidation of xanthene was readily achieved under direct anodic oxidation. The reactivity of benzamides was significantly enhanced by the virtue of the solvent effect of hexafluoroisopropanol (HFIP). An obvious hydrogen bonding between HFIP and benzamide was detected, and the proton-coupled electron-transfer (PCET) effect was proposed for the enhancement effect of HFIP. In this transformation, a broad range of primary and secondary amides were readily used as amidating reagents, including l-proline-, naproxen-, and probencid-derived amides. We proposed a plausible reaction mechanism for this direct amidation based on the experimental observations.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"60 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135552864","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}
Lei Zhan, Qian Wang, Haitao Tang, Zu-Yu Mo, Ying-Ming Pan
Organoselenium compounds are crucial molecules extensively utilized in diverse fields such as medicine, agriculture, catalysis, and organic materials. The incorporation of selenium atoms into organic molecules holds significant importance in synthetic chemistry. Organic electrochemical synthesis, a green, mild, and efficient strategy, has displayed remarkable potential for organoselenium chemistry synthesis. Consequently, there has been substantial interest in recent years in researching electrochemically mediated synthesis of organoselenium compounds. This review provides an overview of the progress made in electrochemically mediated organic selenium reactions over the last decade, including electrochemical mediated selenium catalysis, electrochemical oxidation of diselenides coupling, and electrochemical oxidation tandem selenocyclization. The scope, limitations, and mechanisms of those reactions were emphasized.
{"title":"Recent Advances in Electrochemically Mediated Reaction of Diselenides","authors":"Lei Zhan, Qian Wang, Haitao Tang, Zu-Yu Mo, Ying-Ming Pan","doi":"10.1055/a-2169-3807","DOIUrl":"https://doi.org/10.1055/a-2169-3807","url":null,"abstract":"Organoselenium compounds are crucial molecules extensively utilized in diverse fields such as medicine, agriculture, catalysis, and organic materials. The incorporation of selenium atoms into organic molecules holds significant importance in synthetic chemistry. Organic electrochemical synthesis, a green, mild, and efficient strategy, has displayed remarkable potential for organoselenium chemistry synthesis. Consequently, there has been substantial interest in recent years in researching electrochemically mediated synthesis of organoselenium compounds. This review provides an overview of the progress made in electrochemically mediated organic selenium reactions over the last decade, including electrochemical mediated selenium catalysis, electrochemical oxidation of diselenides coupling, and electrochemical oxidation tandem selenocyclization. The scope, limitations, and mechanisms of those reactions were emphasized.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47454094","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}
An efficient, cost-effective, easy and green method is reported for the preparation of N,N’-alkyl aryl ureas and N,N’-dialkylureas via carbamates. This improved procedure is devoid of any hazardous reagents such as phosgent, isocyanates etc. and has shown a broad substrate scope with good to excellent yields. As compared to literature reports, this procedure is operationally simple, potentially scalable and significantly benign to synthesize these important motifs.
{"title":"IMPROVED SYNTHESIS OF UNSYMMETRICAL UREAS VIA N-ALKYL CARBAMATES","authors":"Prachi Ramteke, Dinesh Kumar Tanwar, M. Gill","doi":"10.1055/a-2157-5925","DOIUrl":"https://doi.org/10.1055/a-2157-5925","url":null,"abstract":"An efficient, cost-effective, easy and green method is reported for the preparation of N,N’-alkyl aryl ureas and N,N’-dialkylureas via carbamates. This improved procedure is devoid of any hazardous reagents such as phosgent, isocyanates etc. and has shown a broad substrate scope with good to excellent yields. As compared to literature reports, this procedure is operationally simple, potentially scalable and significantly benign to synthesize these important motifs.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48992525","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}
Liqaa A. Mohammed, Mohammed Alwan Farhan, Safaa A. Dadoosh, Mustafa A. Alheety, Abdulwahhab H. Majeed, Ali Saadon Mahmood, Zaid H. Mahmoud
Benzimidazole is a heterocyclic compound formed by fusing the benzene ring with an imidazole ring that contains two nitrogen atoms. Benzimidazole and its derivatives are prepared in different ways, including condensation of o-phenylenediamine with carbonyl compounds (aldehydes and ketones) or with carboxylic acids and their derivatives. The benzimidazoles can also be prepared by rearranging other heterocyclic compounds such as quinoxaline derivatives, triazole derivatives, etc. In recent decades, benzimidazoles were prepared using green methods such as microwaves, ultrasound, and the use of an environmentally friendly catalyst, as well as photochemical reactions. Benzimidazoles have attracted the interest of scientists and researchers due to the great medical efficacy shown by them for various diseases. The benzimidazole derivatives show many pharmacological activities such as anticancer, anti-inflammatory, antioxidant, anticoagulant, antiviral, etc. This review focuses on shedding light on benzimidazole and its derivatives, the most important methods used to prepare it, as well as the biological applications in our daily lives.
{"title":"A Review on Benzimidazole Heterocyclic Compounds: Synthesis and their Medicinal Activity Applications","authors":"Liqaa A. Mohammed, Mohammed Alwan Farhan, Safaa A. Dadoosh, Mustafa A. Alheety, Abdulwahhab H. Majeed, Ali Saadon Mahmood, Zaid H. Mahmoud","doi":"10.1055/a-2155-9125","DOIUrl":"https://doi.org/10.1055/a-2155-9125","url":null,"abstract":"Benzimidazole is a heterocyclic compound formed by fusing the benzene ring with an imidazole ring that contains two nitrogen atoms. Benzimidazole and its derivatives are prepared in different ways, including condensation of o-phenylenediamine with carbonyl compounds (aldehydes and ketones) or with carboxylic acids and their derivatives. The benzimidazoles can also be prepared by rearranging other heterocyclic compounds such as quinoxaline derivatives, triazole derivatives, etc. In recent decades, benzimidazoles were prepared using green methods such as microwaves, ultrasound, and the use of an environmentally friendly catalyst, as well as photochemical reactions. Benzimidazoles have attracted the interest of scientists and researchers due to the great medical efficacy shown by them for various diseases. The benzimidazole derivatives show many pharmacological activities such as anticancer, anti-inflammatory, antioxidant, anticoagulant, antiviral, etc. This review focuses on shedding light on benzimidazole and its derivatives, the most important methods used to prepare it, as well as the biological applications in our daily lives.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"67 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41257164","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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