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Electrochemical Generation of Ketyl Radicals and Their Applications 电化学生成酮基自由基及其应用
IF 2.5
SynOpen Pub Date : 2024-03-18 DOI: 10.1055/a-2280-0055
Zhoumei Tan, Kun Xu, Chengchu Zeng
{"title":"Electrochemical Generation of Ketyl Radicals and Their Applications","authors":"Zhoumei Tan, Kun Xu, Chengchu Zeng","doi":"10.1055/a-2280-0055","DOIUrl":"https://doi.org/10.1055/a-2280-0055","url":null,"abstract":"<p>Ketyl radicals display new reactivities beyond the intrinsic electrophilicity of carbonyls. Recent progress in organic electrosynthesis has fueled the generation and utilization of ketyl radicals under ‘greener’ conditions. This graphical review summarizes these electrochemical advancements into three major categories: cross-pinacol couplings, coupling of carbonyls with alkyl radical precursors, and coupling of carbonyls with unsaturated systems (alkenes, alkynes, cyanoarenes, and N-heterocycles).</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"43 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140168794","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}
引用次数: 0
Regioselective C3-Formylation of 2H-Indazoles Using Selectfluor under Microwave-Assisted Conditions 微波辅助条件下使用 Selectfluor 对 2H-Indazoles 进行区域选择性 C3-甲酰化反应
IF 2.5
SynOpen Pub Date : 2024-03-04 DOI: 10.1055/a-2266-3213
Manivel Pitchai, Mahammed Kaspady, Gopikumar Indasi, Rajesh Krishnan, Gururaju Sannakki Maheswarappa, Muthalagu Vetrichelvan, Arvind Mathur, Anuradha Gupta
{"title":"Regioselective C3-Formylation of 2H-Indazoles Using Selectfluor under Microwave-Assisted Conditions","authors":"Manivel Pitchai, Mahammed Kaspady, Gopikumar Indasi, Rajesh Krishnan, Gururaju Sannakki Maheswarappa, Muthalagu Vetrichelvan, Arvind Mathur, Anuradha Gupta","doi":"10.1055/a-2266-3213","DOIUrl":"https://doi.org/10.1055/a-2266-3213","url":null,"abstract":"<p>An efficient microwave-assisted Selectfluor-mediated regioselective C3-formylation of 2<i>H</i>-indazoles bearing a variety of alkyl and aryl substituents using DMSO as the formylating agent has been developed. This methodology provides access to 3-formyl 2<i>H</i>-indazoles with moderate to excellent yields. These functionalized indazoles are potentially useful as templates for drug discovery. Control experimental results suggest that this formylation probably proceeds through a radical pathway.</p>","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"3 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140034633","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}
引用次数: 0
Synthesis of 3,4-Disubstituted Pyrroline Nitroxides Containing Diphenylphosphane or Diphenylphosphane Oxide Substituents 含二苯基膦或二苯基膦氧化物取代基的 3,4-二取代吡咯啉氮氧化物的合成
IF 2.5
SynOpen Pub Date : 2024-03-01 DOI: 10.1055/a-2264-8302
Áron Balázsi, Balázs Bognár, József Jekő, Tamás Kálai
{"title":"Synthesis of 3,4-Disubstituted Pyrroline Nitroxides Containing Diphenylphosphane or Diphenylphosphane Oxide Substituents","authors":"Áron Balázsi, Balázs Bognár, József Jekő, Tamás Kálai","doi":"10.1055/a-2264-8302","DOIUrl":"https://doi.org/10.1055/a-2264-8302","url":null,"abstract":"<p>(Methyl 4-(diphenylphosphoryl)-2,2,5,5-tetramethyl-2,5-dihydro-1<i>H</i>-pyrrole-3-carboxylate-1-yl)oxydanyl was obtained as a key intermediate of the reaction starting from 3,4-dibromo-2,2,5,5-tetramethyl-2,5-dihydro-1<i>H</i>-pyrrol-1-yloxydanyl or (methyl 2,2,5,5-tetramethyl-2,5-dihydro-1<i>H</i>-pyrrole-3-carboxylate-1-yl)oxidanyl. This key compound could be converted into an azido-specific Staudinger ligation-inducing spin label, amino- and thiol-specific spin label, or MITO-CP-like antiproliferative agent.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"54 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140017348","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}
引用次数: 0
Synthesis of C-Glucoside Analogues of Naturally Occurring Phenyl­ethanoid O-Glucosides 天然苯乙醇 O-葡萄糖苷的 C-葡萄糖苷类似物的合成
IF 2.5
SynOpen Pub Date : 2024-01-25 DOI: 10.1055/s-0042-1751553
Amudala Subramanyam, Sumit Sumit, Indrapal S. Aidhen
{"title":"Synthesis of C-Glucoside Analogues of Naturally Occurring Phenyl­ethanoid O-Glucosides","authors":"Amudala Subramanyam, Sumit Sumit, Indrapal S. Aidhen","doi":"10.1055/s-0042-1751553","DOIUrl":"https://doi.org/10.1055/s-0042-1751553","url":null,"abstract":"<p>Structural modifications of natural products has been a highly effective approach in the search for new leads with improved biological activity, aqueous solubility, and stability. Phenylethanoid glycosides (PEGs), as natural compounds, have attracted great attention due to their promising biological activities. These activities include neuroprotection, antioxidant, immunoregulation, anti-inflammatory, and analgesic effects, as well as antitumor, antiviral, and hepatoprotective abilities. Three potent PEGs, acteoside, echinacoside, and salidroside, are gaining renewed interest in this class of compounds. However, being <i>O</i>-glycosides, PEGs have low bioavailability due to factors such as poor intestinal permeability and low hydrolytic stability. The promising pharmacological properties and the limitations have inspired us to synthesize <i>C</i>-analogues that are expected to be hydrolytically stable.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"42 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139587118","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}
引用次数: 0
Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition 通过叠氮-炔烃环加成法合成具有生物活性的 1,2,3-三唑融合大环
IF 2.5
SynOpen Pub Date : 2024-01-04 DOI: 10.1055/a-2212-0996
{"title":"Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition","authors":"","doi":"10.1055/a-2212-0996","DOIUrl":"https://doi.org/10.1055/a-2212-0996","url":null,"abstract":"A systematic highlight of syntheses reported since 2006 of 1,2,3-triazole-fused macrocycles possessing biological activities such as anticancer, antibacterial, antiviral, anti-inflammatory and antilarval action, is presented in this review. The well-renowned Cu-catalyzed azide-alkyne cycloaddition reaction was noted to be highly efficient and is one the most common methods utilized by scientists for the synthesis of 1,4-disubstituted triazole-fused macrocycles, whereas Ru-catalyzed cycloaddition is common for the formation of 1,5-disubstituted bioactive triazoles. This review would thus be extremely beneficial for both synthetic organic and medicinal chemists.1 Introduction2 Anticancer Derivatives3 Antibacterial Derivatives4 Derivatives with Dual Activity5 Antilarval Derivatives6 Anti-inflammatory Derivatives7 Antiviral Derivatives8 Anti-trypanosomal Derivatives9 Derivatives with Miscellaneous Activities10 Conclusion","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"16 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139105337","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}
引用次数: 0
Synthesis of Propellane-Type 5/5/6-Tricyclic System via Tandem-Metathesis: A New Approach to Quadranoid Skeleton 通过串联甲基化反应合成丙烷型 5/5/6 三环系统：四面体骨架的新方法
IF 2.5
SynOpen Pub Date : 2023-12-28 DOI: 10.1055/a-2236-0803
S. Kotha, R. Keesari
{"title":"Synthesis of Propellane-Type 5/5/6-Tricyclic System via Tandem-Metathesis: A New Approach to Quadranoid Skeleton","authors":"S. Kotha, R. Keesari","doi":"10.1055/a-2236-0803","DOIUrl":"https://doi.org/10.1055/a-2236-0803","url":null,"abstract":"We disclose a useful synthetic study to prepare a propellane-type 5/5/6-tricyclic system which is present in diquinane-based natural products such as quadrone, terrecyclic acid A, terrecyclol, etc. The present methodology involves LDA-mediated regio- and stereoselective allylation, and tandem-metathesis as key steps. The target molecules were assembled in just two steps starting from a readily available building block, 3β-vinyl-tricyclic ketone, which is prepared from endo-dicyclopentadiene-1-one. All the compounds prepared here are characterized by NMR data analysis and/or chemical methods. The synthetic studies demonstrated here are useful in the synthesis of quadronoid type of natural products.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"57 12","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139150903","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}
引用次数: 0
Oxidation of Alcohols to Aldehydes and Ketones Using a Catalytic Pairing of a Nitroxide and Nitric Acid 利用氧化氮和硝酸的催化配对将醇氧化成醛和酮
IF 2.5
SynOpen Pub Date : 2023-12-21 DOI: 10.1055/a-2217-9577
Manisha Sharma, Arturo León Sandoval, Nicholas E. Leadbeater
{"title":"Oxidation of Alcohols to Aldehydes and Ketones Using a Catalytic Pairing of a Nitroxide and Nitric Acid","authors":"Manisha Sharma, Arturo León Sandoval, Nicholas E. Leadbeater","doi":"10.1055/a-2217-9577","DOIUrl":"https://doi.org/10.1055/a-2217-9577","url":null,"abstract":"<p>A methodology for the oxidation of alcohols to aldehydes and ketones is presented. The approach employs catalytic quantities of a nitroxide and nitric acid, with no additives or metal catalysts being required. It proves effective for a range of aromatic, heteroaromatic, and aliphatic alcohol substrates, the desired products being formed in good to excellent yield. In the case of primary alcohols, the oxidation can be stopped at the aldehyde without concomitant formation of the corresponding carboxylic acid.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"5 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-12-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139028221","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}
引用次数: 0
Low Molecular Weight Supramolecular Allobetuline-, Cyclohexanol-, or Undecanol-Appended 1,2,3-Triazole-Based Gelators: Synthesis and Molecular Dynamics Simulation Study 低分子量超分子阿洛贝图林、环己醇或十一烷醇添加的 1,2,3 三唑基凝胶剂：合成与分子动力学模拟研究
IF 2.5
SynOpen Pub Date : 2023-12-18 DOI: 10.1055/s-0040-1720100
Victoria Lipson, Oleg Zhikol, Svetlana Shishkina, Alexander Semenenko, Karina Kulyk, Pavel Mateychenko, Vladimir Musatov, Alexander Mazepa, Vladimir Vakula, Alexander Borisov, Alexander Kyrychenko
{"title":"Low Molecular Weight Supramolecular Allobetuline-, Cyclohexanol-, or Undecanol-Appended 1,2,3-Triazole-Based Gelators: Synthesis and Molecular Dynamics Simulation Study","authors":"Victoria Lipson, Oleg Zhikol, Svetlana Shishkina, Alexander Semenenko, Karina Kulyk, Pavel Mateychenko, Vladimir Musatov, Alexander Mazepa, Vladimir Vakula, Alexander Borisov, Alexander Kyrychenko","doi":"10.1055/s-0040-1720100","DOIUrl":"https://doi.org/10.1055/s-0040-1720100","url":null,"abstract":"<p>Three novel isomeric supramolecular allobetuline-appended 1,2,3-triazole-based potential gelators and two model compounds with cyclohexanol or undecanol fragments in the structure instead of the triterpenoid platform were synthesized. Their ability to form gels in different solvents was studied experimentally and computationally by molecular dynamics simulations and quantum chemical calculations. We found that the gelling ability of such compounds is driven by the binding energy of intermolecular tail substituent interactions. The less significant factor is the molecule unfolding in a solvent, providing that the gelling substance is actually soluble. Preferred unfolded conformations were identified by classical molecular dynamics simulation and suggested the most prospective 1,2,3-triazole-based potential gelators.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"3 6 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138745884","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}
引用次数: 0
Recent Developments in the Detection of Zn2+ Ions Using Schiff Base Probes 使用希夫碱探针检测 Zn2+ 离子的最新进展
IF 2.5
SynOpen Pub Date : 2023-12-18 DOI: 10.1055/a-2211-2692
Ram Kumar, Bholey Singh, Shwetank Shashi Pandey, Balaram Pani
{"title":"Recent Developments in the Detection of Zn2+ Ions Using Schiff Base Probes","authors":"Ram Kumar, Bholey Singh, Shwetank Shashi Pandey, Balaram Pani","doi":"10.1055/a-2211-2692","DOIUrl":"https://doi.org/10.1055/a-2211-2692","url":null,"abstract":"<p>In the past few decades, zinc has attracted great attention from the scientific community due to its supreme importance in living organisms. Zinc is a trace element that is vitally important to all living organisms and it plays an important role in the immune system, wound healing, growth, and division. Therefore, the development and advancement of simple, efficient, selective, and inexpensive chemosensors for the determination of Zn<sup>2+</sup> is a paramount prerequisite. Chemosensors have unique properties that are used for the specific and selective determination of several metal ions. This review summarizes the Schiff base chemosensors designed and synthesized by several research groups from the year 2018. The interaction of these probes with zinc metal ions has also been discussed briefly in this review. Furthermore, the comparison of detection limits of these probes demonstrated that the Schiff base probe possessing two benzothiazole moieties exhibits the lowest detection limit (0.00028 μM), indicating it to be the lead compound in the determination of Zn<sup>2+</sup> ions in the near future.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"305 3 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138741013","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}
引用次数: 0
tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes 叔丁氧羰基介导的 α-季均苯甲醛原醛脱羰基反应
IF 2.5
SynOpen Pub Date : 2023-12-18 DOI: 10.1055/a-2231-3108
Ben Stokes, Xiaofeng Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco
{"title":"tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes","authors":"Ben Stokes, Xiaofeng Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco","doi":"10.1055/a-2231-3108","DOIUrl":"https://doi.org/10.1055/a-2231-3108","url":null,"abstract":"\u0000 Tert-butoxide mediates the Haller–Bauer-type (protodeformylative) decarbonylation of readily accessed α-quaternary homobenzaldehydes and related compounds at room temperature, generating cumene products. Both geminal dialkyl and geminal diaryl substituents are tolerated. Gem-dimethyls are sufficient for decarbonylation of polycyclic arenyl substrates whereas monocyclic aromatic homobenzaldehydes require cyclic gem-dialkyls or gem-diaryls for significant decarbonylation.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" 38","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138963761","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}
引用次数: 0
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