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Recent Developments on the Synthesis of Sulfoxides via Sulfenate Anions 硫酸盐阴离子法合成亚砜的研究进展
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-18 DOI: 10.1055/a-2155-3498
Fumito Saito
{"title":"Recent Developments on the Synthesis of Sulfoxides via Sulfenate Anions","authors":"Fumito Saito","doi":"10.1055/a-2155-3498","DOIUrl":"https://doi.org/10.1055/a-2155-3498","url":null,"abstract":"Since the early 2000s, novel synthetic methods for the preparation of sulfoxides have emerged that involve sulfenate anions as sulfur nucleophiles. This short review showcases key advances in these sulfenate protocols, including catalytic enantioselective alkylation and arylation, and provides future directions for this research field.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"10 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87435116","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
SYNFORM ISSUE 2023/8 Synform issue 2023/8
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-17 DOI: 10.1055/s-0040-1720605
M. Zanda
{"title":"SYNFORM ISSUE 2023/8","authors":"M. Zanda","doi":"10.1055/s-0040-1720605","DOIUrl":"https://doi.org/10.1055/s-0040-1720605","url":null,"abstract":"using thioanisole and p -toluenesulfonamide as test substrates. Indeed, selective formation of the sulfilimine was observed when bromide was used as the mediator and MeOH as the base. In addition, bromide and MeOH also served as supporting electrolyte and solvent, which allowed for an extremely efficient use of the reactants.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"4 1","pages":"A133 - A148"},"PeriodicalIF":2.6,"publicationDate":"2023-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84443103","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5- b ]indoles and Related Heterocycles 2-(三氯甲基)-5-苯基嘧啶的硝基环化:在2-(三氯甲基)嘧啶[4,5- b]吲哚及相关杂环合成中的应用
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-14 DOI: 10.1055/a-2159-1611
Ulises Jose Vargas-Cruz, José G. Peralta-Chávez, Misael A. Romero-Reyes, D. Martínez-Otero, M. Romero-Ortega
{"title":"Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5- b ]indoles and Related Heterocycles","authors":"Ulises Jose Vargas-Cruz, José G. Peralta-Chávez, Misael A. Romero-Reyes, D. Martínez-Otero, M. Romero-Ortega","doi":"10.1055/a-2159-1611","DOIUrl":"https://doi.org/10.1055/a-2159-1611","url":null,"abstract":"An aromatic C–H nitrene insertion of 2-trichloromethylpyrimidines bearing a phenyl substituent in C-5 position is described. Treatment of 2-trichloromethyl-4-chloro-5-phenylpyrimidines with sodium azide in DMF or the reflux of 2-trichloromethyl-4-azido-5-phenylpyrimidines in toluene provided 2-trichloromethylpyrimido[4,5-b]indole derivatives in moderate yields. Excellent yields of this heterocyclic systems were obtained through of the aromatic C–H insertion with Du Bois catalyst. This is an attractive approach for synthesizing pyrimido[4,5-b]indoles with a trichloromethyl substituent in the pyrimidine moiety.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"72 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84105050","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
New Route to Direct Synthesis of Symmetrical Ureas from Carboxylic Acids 羧酸直接合成对称脲的新途径
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-13 DOI: 10.1055/a-2172-8329
Daniel Jahani, H. Yassine, Mostafa Khouili, M. D. Pujol
{"title":"New Route to Direct Synthesis of Symmetrical Ureas from Carboxylic Acids","authors":"Daniel Jahani, H. Yassine, Mostafa Khouili, M. D. Pujol","doi":"10.1055/a-2172-8329","DOIUrl":"https://doi.org/10.1055/a-2172-8329","url":null,"abstract":"ABSTRACT: The first method for the direct conversion of carboxylic acids into ureas has been developed. The classical procedures described above for the formation of ureas from carboxylic acids require two steps, preparation of the isocyanate followed by its aminolysis. In this work, arylcarboxylic and arylalkylcarboxylic acids have been transformed into symmetric ureas in a single step using DPPA or sodium azide as nitrogen source. The addition of water (method A) or the presence of solvent water (method B) was essential for the formation of symmetrical ureas from the corresponding carboxylic acids. The corresponding ureas have been obtained in good to excellent yields of 46 to 100%. This procedure was compatible with differ-ent substituents present in the starting carboxylic acid.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"68 6 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76495965","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Zinc-Mediated C–H Metalations in Modern Organic Synthesis 现代有机合成中锌介导的C-H金属化
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-10 DOI: 10.1055/a-2155-3423
Daria Karolina Wanic, Rebecca Melvin, G. Barker
{"title":"Zinc-Mediated C–H Metalations in Modern Organic Synthesis","authors":"Daria Karolina Wanic, Rebecca Melvin, G. Barker","doi":"10.1055/a-2155-3423","DOIUrl":"https://doi.org/10.1055/a-2155-3423","url":null,"abstract":"C-H deprotometalations have long occupied a key role in modern organic synthesis in both the research laboratory and pharmaceutical and fine chemical manufacture, thanks to readily accessible reagents and well-established procedures. Typically, organolithiums are the reagent of choice thanks to high reactivity and ease of use but these are incompatible with base- and nucleophile-sensitive functional groups. In comparison, organozinc base complexes offer a milder approach to deprotonative C-H functionalisations, and compatibility with a wide range of functionalities which would be problematic when using the alternative organolithium or organomagnesium reagents has now been demonstrated. Here, we review the current state of the art in zinc-mediated C-H metalations at substituted arenes, heteroarenes and Csp3-H sites.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"18 1","pages":"3487 - 3501"},"PeriodicalIF":2.6,"publicationDate":"2023-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82193134","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines 可见光介导双氧氧化1-苄基-3,4-二氢异喹啉:1-苯甲酰异喹啉和1-苯甲酰-3,4-二氢异喹啉的可切换合成
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-10 DOI: 10.1055/a-2160-8903
Peipei Ma, Hongli Wu, H. Gan
{"title":"Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines","authors":"Peipei Ma, Hongli Wu, H. Gan","doi":"10.1055/a-2160-8903","DOIUrl":"https://doi.org/10.1055/a-2160-8903","url":null,"abstract":"A visible-light-mediated metal-free oxidation of 1-BnDHIQs to switchable preparation of BzIQs and BzDHIQs has been realized in which dioxygen as an oxidant. 6,7-Dialkoxy BzIQs and BzDHIQs were comprehensively synthesized in this protocol. This protocol provides a facile route for the efficient synthesis of isoquinoline alkaloids. Mechanistic investigation suggested that radical pathway and ionic pathway may exist simultaneously and intermediate A may be the key compound for the formation of the products.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"1 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76957653","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
C-5 Epimerisation of d -Mannopyranosyl Fluorides: The Influence of Anomeric Configuration on Radical Reactivity d -甘露吡喃基氟化物的C-5外映反应:异端构型对自由基反应性的影响
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-10 DOI: 10.1055/a-2149-4586
Nicholas W. See, G. Pierens, E. Krenske, V. Ferro
{"title":"C-5 Epimerisation of d -Mannopyranosyl Fluorides: The Influence of Anomeric Configuration on Radical Reactivity","authors":"Nicholas W. See, G. Pierens, E. Krenske, V. Ferro","doi":"10.1055/a-2149-4586","DOIUrl":"https://doi.org/10.1055/a-2149-4586","url":null,"abstract":"The fluorine-directing effect has so far been exploited to provide short and efficient synthetic routes to rare L-ido sugars. However, the importance of anomeric configuration to its success has remained experimentally unverified. We now report on the synthesis of α- and β-configured per-O-benzoylated mannopyranosyl fluorides and initially show that their reactivity towards photo-bromination is strongly dependent on the anomeric configuration. The stereochemical basis of the fluorine-directing effect is then validated by revealing the striking difference in stereoselectivity observed for the free radical reductions of the isolated 5-C-bromo sugars. This work importantly provides a synthetic route to a donor-functionalised derivative of L-gulose and reveals new insights into the behaviour of glycosyl radicals.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"31 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82424639","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cobalt-Catalyzed Enantioselective Alkynylation of Oxabicyclic Alkenes 钴催化氧三环烯烃的对映选择性炔基化
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-07 DOI: 10.1055/a-2152-0355
Lin-Wen Wei, Zhan-Cai Ma, Zhao Wang, Yu Zhao, Yuan Huang
{"title":"Cobalt-Catalyzed Enantioselective Alkynylation of Oxabicyclic Alkenes","authors":"Lin-Wen Wei, Zhan-Cai Ma, Zhao Wang, Yu Zhao, Yuan Huang","doi":"10.1055/a-2152-0355","DOIUrl":"https://doi.org/10.1055/a-2152-0355","url":null,"abstract":"An efficient access to enantioenriched cyclic homopropargylic alcohols through an unprecedented cobalt-catalyzed asymmetric alkynylation of oxabicyclic alkenes. By using inexpensive cobalt salt/chiral bisphosphine ligand as the catalyst and easy-to-handle potassium alkynyltrifluoroborates as the nucleophiles, synthetically valuable homopropargylic alcohols are obtained in moderate to good yields and high enantioselectivities.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"16 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81466542","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Glycosyl Triazole Based Pyridinamide/CuI-Catalyzed Coupling of 2-Halobenzamides with Active Methylene Compounds 糖基三唑吡啶酰胺/ cu催化2-卤代苯酰胺与活性亚甲基化合物的偶联
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-06 DOI: 10.1055/a-2157-9001
Sumit Kumar Singh, Sunil Kumar, Mangal S Yadav, S. Bhattacharya, V. Tiwari
{"title":"Glycosyl Triazole Based Pyridinamide/CuI-Catalyzed Coupling of 2-Halobenzamides with Active Methylene Compounds","authors":"Sumit Kumar Singh, Sunil Kumar, Mangal S Yadav, S. Bhattacharya, V. Tiwari","doi":"10.1055/a-2157-9001","DOIUrl":"https://doi.org/10.1055/a-2157-9001","url":null,"abstract":"The report describes a convenient method for the Cu(I)-catalyzed tandem synthesis of dihydrophenanthridine-diones and substituted isoquinolinones with the assistance of efficient glycosyl 1,2,3-triazole-based pyridinamide ligands. The catalytic system effectively works for the coupling of N-substituted 2-halobenzamides with various active methylene compounds to achieve a high-to-excellent yield of biologically relevant heterocyclic scaffolds. The consecutive path of the reaction including intermolecular C-C cross-coupling followed by intramolecular cyclization efficiently takes place at low catalytic loading. These glycosyl triazole-appended pyridinamides were synthesized in good yields via CuI/DIPEA mediated regioselective CuAAC click tool. There are some notable features of the method, including low catalytic loading, the cost-effective and biocompatible nature of ligands, high reaction yield, and easily accessible starting materials that make the protocol more versatile.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"98 9 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83324781","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Stereoselective Synthesis of Highly Functionalized Aminobenzothiazole-Fused Spirooxindole Derivatives: in silico and in vitro Anti-Diabetic Studies 立体选择性合成高功能化氨基苯并噻唑-融合螺菌吲哚衍生物:在硅和体外抗糖尿病研究
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-04 DOI: 10.1055/a-2161-0283
Narayanasamy Nivetha, Shashank M. Patil, R. Ramu, S. Sreenivasa, S. Velmathi
{"title":"Stereoselective Synthesis of Highly Functionalized Aminobenzothiazole-Fused Spirooxindole Derivatives: in silico and in vitro Anti-Diabetic Studies","authors":"Narayanasamy Nivetha, Shashank M. Patil, R. Ramu, S. Sreenivasa, S. Velmathi","doi":"10.1055/a-2161-0283","DOIUrl":"https://doi.org/10.1055/a-2161-0283","url":null,"abstract":"A higly functionalized spirooxindole pyrrolizidine/pyrrolothiazole derivatives has been synthesised by the three-component 1,3-dipolar cycloaddition reaction of benzothiazolyl amides with isatin-based azomethine ylides. The pharmacologically significant spirooxindole derivatives bearing one quaternary carbon and four stereocentres were obtained in excellent yields (up to 93 %). The compounds were screened for their anti-diabetic activity against two enzymes, α-glucosidase and α-amylase. The results exhibited potent inhibitory activity against these enzymes, especially compound 6b, which showed excellent activity compared to the standard acarbose. Molecular docking against the receptors showed excellent interactions of the synthesized compounds in a similar way to acarbose. Further, the docking results of compound 6b evinced the strong binding interactions of the compound with the receptors. Additionally, molecular dynamics simulations were carried out and confirmed the stability of compound 6b in the active pockets of enzymes over 100 ns.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"205 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84234266","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","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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