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Erratum - Designing the Secondary Coordination Sphere in Small-Molecule Catalysis 勘误 - 设计小分子催化中的二级配位层
Synlett Pub Date : 2024-04-01 DOI: 10.1055/s-0043-1763761
Inbal L. Zak, Santosh C. Gadekar, Anat Milo
{"title":"Erratum - Designing the Secondary Coordination Sphere in Small-Molecule Catalysis","authors":"Inbal L. Zak, Santosh C. Gadekar, Anat Milo","doi":"10.1055/s-0043-1763761","DOIUrl":"https://doi.org/10.1055/s-0043-1763761","url":null,"abstract":"","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"77 8","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140759028","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 advances in the synthesis of C-Aryl-glycosides since 2019 2019 年以来 C-芳基苷合成的最新进展
Synlett Pub Date : 2024-03-07 DOI: 10.1055/a-2283-0623
Jiagen Li, Xuefeng Jiang
{"title":"Recent advances in the synthesis of C-Aryl-glycosides since 2019","authors":"Jiagen Li, Xuefeng Jiang","doi":"10.1055/a-2283-0623","DOIUrl":"https://doi.org/10.1055/a-2283-0623","url":null,"abstract":"C-Aryl-glycosides represent a significant subclass of crucial glycosidic compounds, increasingly capturing the attention of pharmaceutical developers as bioelectronic motifs embedded within glycosides. Their outstanding resistance to enzymatic hydrolysis bestows a distinctive advantage in the field of drug development, particularly in therapeutic domains such as diabetes treatment, where pharmaceuticals based on the C-Aryl-glycosides architecture manifest compelling therapeutic efficacy. As a result, researchers in the realm of synthetic chemistry have diligently explored and devised a plethora of streamlined and efficacious synthetic methodologies. This comprehensive review systematically delineates methodologies employed in recent years for the efficient synthesis of C-Aryl-glycosides, offering insights into three primary directions: transition metal catalysis, radical strategies, and metal-free catalysis process.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"5 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140077502","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
Practical Method for the Synthesis of Mesoionic 1,3-Diaryltetrazolium Derivatives Bearing a Para-substituted Phenyl Group at the 1- or 3-Position from Anilines 用苯胺合成在 1 位或 3 位上带有对位取代苯基的介离子 1,3-二叔基四氮唑衍生物的实用方法
Synlett Pub Date : 2024-03-07 DOI: 10.1055/a-2283-5749
Yuta Matsukawa, T. Hirashita
{"title":"Practical Method for the Synthesis of Mesoionic 1,3-Diaryltetrazolium Derivatives Bearing a Para-substituted Phenyl Group at the 1- or 3-Position from Anilines","authors":"Yuta Matsukawa, T. Hirashita","doi":"10.1055/a-2283-5749","DOIUrl":"https://doi.org/10.1055/a-2283-5749","url":null,"abstract":"A simple, economical, and safe method for the synthesis of mesoionic 1,3-diaryltetrazolium derivatives bearing a p-substituted phenyl group at the 1- or 3-position via thiosemicarbazides was established. Such compounds were directly obtained from the corresponding p-substituted anilines instead of aryl isothiocyanates and arylhydrazines. The newly synthesized mesoionic compounds were successfully converted into the corresponding nitrosotetrazolium salts, which were utilized as catalysts for oxidation of an aliphatic alcohol and analyzed by cyclic voltammetry to determine the correlation between the catalytic efficiencies and redox potentials. The proposed method can be widely applied and is valuable for investigating the substituent effects in mesoionic and related compounds.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"38 23","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140077134","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
Validation and Application of an Innovative Protective Group Concept: Enhancing Substrate Reactivity in Glycosylations by Disrupting Intermolecular Interactions 创新性保护基团概念的验证与应用：通过破坏分子间相互作用增强糖基化过程中的底物反应性
Synlett Pub Date : 2024-02-15 DOI: 10.1055/a-2269-7680
Kumpei Yano, Takuya Yoshimoto, Masato Tsutsui, Y. Manabe, Koichi Fukase
{"title":"Validation and Application of an Innovative Protective Group Concept: Enhancing Substrate Reactivity in Glycosylations by Disrupting Intermolecular Interactions","authors":"Kumpei Yano, Takuya Yoshimoto, Masato Tsutsui, Y. Manabe, Koichi Fukase","doi":"10.1055/a-2269-7680","DOIUrl":"https://doi.org/10.1055/a-2269-7680","url":null,"abstract":"We established an innovative protective approach that disrupts intermolecular interactions to enhance substrate reactivity. Specifically, diacetylimide protection of acetamide prevents the formation of hydrogen bonds, while the incorporation of tert-butyl groups on the aromatic protecting group disrupts π-stacking interactions, both of which culminate in heightened reactivity in glycosylations. We explored the synergistic implementation of these protective measures and implemented applied them to the synthesis of 6-sulfo sialyl Lewis X.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"248 ","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139833535","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
Validation and Application of an Innovative Protective Group Concept: Enhancing Substrate Reactivity in Glycosylations by Disrupting Intermolecular Interactions 创新性保护基团概念的验证与应用：通过破坏分子间相互作用增强糖基化过程中的底物反应性
Synlett Pub Date : 2024-02-15 DOI: 10.1055/a-2269-7680
Kumpei Yano, Takuya Yoshimoto, Masato Tsutsui, Y. Manabe, Koichi Fukase
{"title":"Validation and Application of an Innovative Protective Group Concept: Enhancing Substrate Reactivity in Glycosylations by Disrupting Intermolecular Interactions","authors":"Kumpei Yano, Takuya Yoshimoto, Masato Tsutsui, Y. Manabe, Koichi Fukase","doi":"10.1055/a-2269-7680","DOIUrl":"https://doi.org/10.1055/a-2269-7680","url":null,"abstract":"We established an innovative protective approach that disrupts intermolecular interactions to enhance substrate reactivity. Specifically, diacetylimide protection of acetamide prevents the formation of hydrogen bonds, while the incorporation of tert-butyl groups on the aromatic protecting group disrupts π-stacking interactions, both of which culminate in heightened reactivity in glycosylations. We explored the synergistic implementation of these protective measures and implemented applied them to the synthesis of 6-sulfo sialyl Lewis X.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"1 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139774094","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
New heterocyclic organosulfur compounds derived from dithioacetals 源自二硫代乙醛的新型杂环有机硫化合物
Synlett Pub Date : 2024-02-01 DOI: 10.1055/a-2259-3689
Dawid T. Leja, Wojciech J. Depa, Piotr A. Guńka, J. Zachara, Jaromir B. Lechowicz, G. Groszek
{"title":"New heterocyclic organosulfur compounds derived from dithioacetals","authors":"Dawid T. Leja, Wojciech J. Depa, Piotr A. Guńka, J. Zachara, Jaromir B. Lechowicz, G. Groszek","doi":"10.1055/a-2259-3689","DOIUrl":"https://doi.org/10.1055/a-2259-3689","url":null,"abstract":"The dithioacetalization of lactaldehyde derivatives with ethane-1,2-, propane-1,3-; butane-1,4- and pentane-1,5-dithiols in the presence of 4 mol% of scandium triflate has been described. A series of cyclic dithioacetals were obtained with yields ranging from quantitative to 37%. The dithioacetalization of lactaldehyde derivatives with butane-1,4-dithiol and pentane-1,5-dithiol groups are accompanied by the formation of 14- and 16-membered macrocyclic sulfur structures with yields of 3% and 18%, respectively. In the case of a cyclic dithioacetal derivative with three methylene groups, a diastereoisomeric pair of enantiomers was obtained, the structure of which was confirmed by single-crystal X-ray diffraction analysis. Dithioacetals are useful building blocks in the synthesis of complex chemical structures, macrocyclic compounds can be used to complex metal ions.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"25 3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139876355","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
Spectroscopic Investigation of the Remote C–H Allylation of Amides via Photoredox and Nickel Dual Catalysis 通过光氧化和镍双重催化对酰胺的远程 C-H 烯丙基化的光谱研究
Synlett Pub Date : 2024-02-01 DOI: 10.1055/a-2259-3594
Céline Bourgois, Simon De Kreijger, Bin Xu, U. Tambar, L. Troian‐Gautier
{"title":"Spectroscopic Investigation of the Remote C–H Allylation of Amides via Photoredox and Nickel Dual Catalysis","authors":"Céline Bourgois, Simon De Kreijger, Bin Xu, U. Tambar, L. Troian‐Gautier","doi":"10.1055/a-2259-3594","DOIUrl":"https://doi.org/10.1055/a-2259-3594","url":null,"abstract":"The mechanistic details of a reported allylation reaction were investigated by means of Stern-Volmer experiments and nanosecond transient absorption spectroscopy. Both reference substrates, i.e. allylic chloride and trifluoroacetamide, were inefficient quenchers but large quenching rate constants were observed upon the addition of Ni(COD)2 and bisoxazoline. The large quenching rate constants and absence of observable photoproducts were consistent with a mechanism that operates by energy transfer between the excited-state iridium photosensitizer and the nickel complex.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"64 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139687850","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
New heterocyclic organosulfur compounds derived from dithioacetals 源自二硫代乙醛的新型杂环有机硫化合物
Synlett Pub Date : 2024-02-01 DOI: 10.1055/a-2259-3689
Dawid T. Leja, Wojciech J. Depa, Piotr A. Guńka, J. Zachara, Jaromir B. Lechowicz, G. Groszek
{"title":"New heterocyclic organosulfur compounds derived from dithioacetals","authors":"Dawid T. Leja, Wojciech J. Depa, Piotr A. Guńka, J. Zachara, Jaromir B. Lechowicz, G. Groszek","doi":"10.1055/a-2259-3689","DOIUrl":"https://doi.org/10.1055/a-2259-3689","url":null,"abstract":"The dithioacetalization of lactaldehyde derivatives with ethane-1,2-, propane-1,3-; butane-1,4- and pentane-1,5-dithiols in the presence of 4 mol% of scandium triflate has been described. A series of cyclic dithioacetals were obtained with yields ranging from quantitative to 37%. The dithioacetalization of lactaldehyde derivatives with butane-1,4-dithiol and pentane-1,5-dithiol groups are accompanied by the formation of 14- and 16-membered macrocyclic sulfur structures with yields of 3% and 18%, respectively. In the case of a cyclic dithioacetal derivative with three methylene groups, a diastereoisomeric pair of enantiomers was obtained, the structure of which was confirmed by single-crystal X-ray diffraction analysis. Dithioacetals are useful building blocks in the synthesis of complex chemical structures, macrocyclic compounds can be used to complex metal ions.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"18 3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139816326","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
N-Hetero cyclic carbene catalysis for facile access to Pentasubstituted 4-H Pyran derivatives 利用 N-异环碳烯催化技术轻松获得五代 4-H 吡喃衍生物
Synlett Pub Date : 2024-01-24 DOI: 10.1055/a-2253-4365
Xiaolin Peng, Yulin Wang, Yixian Huang, Sheng Zhang, Zhichao Jin, Shi-Chao Ren
{"title":"N-Hetero cyclic carbene catalysis for facile access to Pentasubstituted 4-H Pyran derivatives","authors":"Xiaolin Peng, Yulin Wang, Yixian Huang, Sheng Zhang, Zhichao Jin, Shi-Chao Ren","doi":"10.1055/a-2253-4365","DOIUrl":"https://doi.org/10.1055/a-2253-4365","url":null,"abstract":"The synthesis of multi-substituted 4-H Pyrans derivatives has drawn considerable attention due to its wide application in agrochemicals, pharmaceuticals, and other functional molecules. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed [3+3] annulation reactions between -ketone esters and enynals for quick access to penta-substituted 4-H Pyran derivatives via a regioselective activation of ynals. A series of 4-H Pyrans derivatives bearing various substituents were obtained in moderate to excellent yields. This method may find further applications in the synthesis of structurally diverse 4-H Pyrans derived functional molecules from readily available starting materials.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"37 11","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139599748","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
An efficient access to heteroaryl/aryl-annulated pyridine derivatives and study of their mosquito larvicidal activity against dengue vector 杂芳基/芳基环化吡啶衍生物的高效获取途径及其对登革热病媒的杀蚊幼虫活性研究
Synlett Pub Date : 2024-01-22 DOI: 10.1055/a-2251-1849
Pamela Pal, Sayanti Show, Sukanya Das, S. Bhakta, Swarupa Mondal, Priya Roy, Tapas Ghosh, Raj Kumar Nandi
{"title":"An efficient access to heteroaryl/aryl-annulated pyridine derivatives and study of their mosquito larvicidal activity against dengue vector","authors":"Pamela Pal, Sayanti Show, Sukanya Das, S. Bhakta, Swarupa Mondal, Priya Roy, Tapas Ghosh, Raj Kumar Nandi","doi":"10.1055/a-2251-1849","DOIUrl":"https://doi.org/10.1055/a-2251-1849","url":null,"abstract":"Herein we report a convergent synthesis of heteroaryl/aryl-annulated pyridine and quinoline derivatives by metal-free Povarov reaction. Para-toluene sulfonic acid has been used as catalyst in this reaction which produced the products in good yields from corresponding aromatic amines and ethyl vinyl ether. Synthesized compounds pyridocoumarin and pyridopyrimidine were evaluated for mosquito larvicidal activity against third instar larvae of Aedes aegypti. Observation on morphological changes in Ae. aegypti (L.) larvae was meant to decide damaged target body part after the treatment with both with pyridocoumarin and pyridopyrimidine at LC50 concentrations.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"37 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139608777","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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