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Synthesis and alpha-Functionalisation of Cyclic Imines 环状胺的合成与 alpha-官能化
Synlett Pub Date : 2024-01-22 DOI: 10.1055/a-2251-4145
Margaret Brimble, Ze Kuang, Xiaobo Ding, D. Furkert
{"title":"Synthesis and alpha-Functionalisation of Cyclic Imines","authors":"Margaret Brimble, Ze Kuang, Xiaobo Ding, D. Furkert","doi":"10.1055/a-2251-4145","DOIUrl":"https://doi.org/10.1055/a-2251-4145","url":null,"abstract":"-Functionalisation of cyclic imines has been explored. The cyclic imine substrates were synthesised from their respective halonitrile precursors using a nucleophilic addition/cyclisation sequence. Selective monohalogenation of the cyclic imines yielded alpha-haloimines, which served as a platform to obtain various alpha-hydroxyimine derivatives. In addition, an unusual tautomerisation and oxidation sequence was observed in the attempted preparation of alpha-hydroxyimines.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"27 13","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139608846","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
Pd-Catalyzed Carbothiolation Using Thioesters with Forming a Quaternary Carbon Pd 催化硫代酯硫代碳化反应，形成季碳
Synlett Pub Date : 2024-01-17 DOI: 10.1055/a-2248-3205
Y. Okura, Ryunosuke Ito, Hyu Kumazawa, Masahisa Nakada
{"title":"Pd-Catalyzed Carbothiolation Using Thioesters with Forming a Quaternary Carbon","authors":"Y. Okura, Ryunosuke Ito, Hyu Kumazawa, Masahisa Nakada","doi":"10.1055/a-2248-3205","DOIUrl":"https://doi.org/10.1055/a-2248-3205","url":null,"abstract":"The Pd-catalyzed carbothiolation using thioesters with forming a quaternary carbon is described. The carbothiolation using thioesters was problematic due to a direct coupling side reaction that produced a sulfide, but this side reaction was successfully suppressed by selecting the thioester and reaction conditions. When chroman and coumaran derivatives were obtained in this reaction, the reactions with S-phenyl 4-methoxybenzothioate, Pd(PPh3)4, and Cs2CO3 at 100 °C in toluene afforded the desired products in good yields (77-92%). The carbothiolation reaction also proceeded using the ester of alkane thiol with higher yields (56-93%) when compared with the previously reported carbothiolation using TIPS thioethers (12-63%). The developed Pd-catalyzed carbothiolation is applicable for the preparation of a wide range of products including a tetralin derivative and an indoline derivative, too. The Pd-catalyzed carbothiolation using thioesters was found to be comparable to previously reported carbothiolation using TIPS thioethers in terms of yield and substrate scope, and to be a superior alternative owing to the stability and lower cost of thioesters.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"115 39","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139616165","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
Harnessing the Power of C-H Functionalization Chemistry to Accelerate Drug Discovery 利用 C-H 功能化化学的力量加速药物研发
Synlett Pub Date : 2024-01-15 DOI: 10.1055/a-2245-6202
Bing Li, S. Tyagarajan, K. Dykstra, Timothy Cernak, Petr Vachal, S. Krska
{"title":"Harnessing the Power of C-H Functionalization Chemistry to Accelerate Drug Discovery","authors":"Bing Li, S. Tyagarajan, K. Dykstra, Timothy Cernak, Petr Vachal, S. Krska","doi":"10.1055/a-2245-6202","DOIUrl":"https://doi.org/10.1055/a-2245-6202","url":null,"abstract":"Abstract The field of C-H functionalization chemistry has experienced rapid growth in the past twenty years, with increasingly powerful applications in organic synthesis. Recognizing the potential of this emerging field to impact drug discovery, a dedicated effort was established in our laboratories more than ten years ago with a goal of facilitating the application of C-H functionalization chemistries to active medicinal chemistry programs. Our approach centered around the strategy of Late-Stage Functionalization (LSF) wherein C−H functionalization chemistry is employed in a systematic and targeted manner to generate high-value analogs from advanced drug leads. To successfully realize this approach, we developed broadly useful LSF chemistry platforms and workflows that increased the success rates of the C-H functionalization chemistries and accelerated access to new derivatives. The LSF strategy, when properly applied, enabled rapid synthesis of molecules designed to address specific medicinal chemistry issues. Several case studies are presented along with descriptions of the group’s platforms and workflows.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":" 10","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139622687","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
Small-molecule Activation by Low-coordinated Germanium Compounds 低配位锗化合物的小分子活化作用
Synlett Pub Date : 2024-01-15 DOI: 10.1055/a-2245-6718
Takahiro Sasamori
{"title":"Small-molecule Activation by Low-coordinated Germanium Compounds","authors":"Takahiro Sasamori","doi":"10.1055/a-2245-6718","DOIUrl":"https://doi.org/10.1055/a-2245-6718","url":null,"abstract":"We have been interested in the differences of properties between low-coordinated carbon compounds and their heavier homologues of group 14 based on e.g., Si and Ge. Fundamental research on the synthesis and characterization of divalent and multiple-bond compounds of heavier group-14 elements has led to a variety of isolated low-coordinated species of heavier group-14 elements that can serve in small-molecule transformations instead of transition metals. The author and his co-workers have focused especially on low-coordinated germanium compounds with double or triple bonds between germanium atoms, and germanium-containing aromatic compounds. Once isolated, the reactivity of these low-coordinated germanium compounds was examined with regard to small-molecule activation. In this account, the reactivity patterns of these compounds will be described.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":" 26","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139621601","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
Acidic Hydrogen-Tethered Electron-Deficient Acceptors for Phosphine-Catalyzed Annulations 用于膦催化猝灭反应的酸性氢系缺电子受体
Synlett Pub Date : 2024-01-10 DOI: 10.1055/a-2242-0543
Leijie Zhou, Hongchao Guo
{"title":"Acidic Hydrogen-Tethered Electron-Deficient Acceptors for Phosphine-Catalyzed Annulations","authors":"Leijie Zhou, Hongchao Guo","doi":"10.1055/a-2242-0543","DOIUrl":"https://doi.org/10.1055/a-2242-0543","url":null,"abstract":"Nucleophilic phosphine-catalyzed annulations are recognized as practical and powerful synthetic tools for various cyclic compounds. Phosphine acceptors play a key role in nucleophilic phosphine catalysis. Design and synthesis of new phosphine acceptors, which are able to introduce new zwitterionic intermediates with new reactivities into the phosphine-catalyzed annulations, are highly desirable. Recently, we applied the proton shift principles in the design of new phosphine acceptors and have developed several phosphine-catalyzed annulation reactions with the use of new phosphine acceptors. In this account, we present a brief introduction of design and application of a series of acidic hydrogen-tethered electron-deficient acceptors for phosphine-catalyzed annulation reactions, categorizing with the atom types (N-H, O-H, C-H) that acidic hydrogen is bounded to.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":" 24","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139627000","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
Applications of Quantum Chemistry in Biomimetic Syntheses of Polycyclic Furanocembrane Derivatives 量子化学在多环呋喃树脂衍生物仿生合成中的应用
Synlett Pub Date : 2024-01-05 DOI: 10.1055/a-2239-6577
Di Wang, Tao Zhou, Jianfeng Ren, Jonathan Hirst, Zhanghua Gao, Bencan Tang
{"title":"Applications of Quantum Chemistry in Biomimetic Syntheses of Polycyclic Furanocembrane Derivatives","authors":"Di Wang, Tao Zhou, Jianfeng Ren, Jonathan Hirst, Zhanghua Gao, Bencan Tang","doi":"10.1055/a-2239-6577","DOIUrl":"https://doi.org/10.1055/a-2239-6577","url":null,"abstract":"This paper summarizes the guidance provided by quantum chemical calculations to the biomimetic syntheses of polycyclic marine furanocembrane derivatives. Polycyclic furanocembrane derivatives are a group of structurally complex and biologically important marine natural products isolated from marine corals. Their syntheses are challenging due to their structural complexity. Biomimetic synthetic proposals have been made and some verified via chemical synthesis. Computational chemistry can support these biomimetic syntheses. Hence, here we describe the synthetic and computational attempts we have made in the biomimetic syntheses of polycyclic furanocembrane derivatives, including intricarene, bielschowskysin, providencin and plumarellide.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"5 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139384233","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
Solvent-Free Synthesis of α-Cyanophosphonates from β-Nitrostyrenes using a Deep Eutectic Solvent 使用深共晶溶剂从 β-硝基苯炔无溶剂合成 α-氰基膦酸盐
Synlett Pub Date : 2024-01-05 DOI: 10.1055/a-2239-6819
Sima Shamsaddinimotlagh, M. Ranjbari, Hossein Tavakol, Min Shi
{"title":"Solvent-Free Synthesis of α-Cyanophosphonates from β-Nitrostyrenes using a Deep Eutectic Solvent","authors":"Sima Shamsaddinimotlagh, M. Ranjbari, Hossein Tavakol, Min Shi","doi":"10.1055/a-2239-6819","DOIUrl":"https://doi.org/10.1055/a-2239-6819","url":null,"abstract":"New α-Cyanophosphonates, which are useful reagents for Horner-Wittig reaction, were synthesized in a solvent-free condition, using choline chloride-zinc chloride deep eutectic solvent (DES) as a catalyst. This work is only the second report on the synthesis of these compounds. In the previous report, diethyltrimethylsilylphosphite was used as a reagent and TiCl4 as a catalyst while in this study, both employed reagent and catalyst (triphenyl phosphine and choline chloride-zinc chloride DES) are cheaper, more available and less harmful than the previous work. Moreover, the reaction involves an interesting cascade reaction between β-nitrostyrenes and two equivalents of triphenylphosphite led to the desired product as a new synthetic route. These compounds can be used in the pharmaceutical and agricultural industries, in addition to their synthetic applications in the preparation of α,β-unsaturated nitriles. The reactions were completed using 20 mol% of DES at 80 °C in 6 hours. 10 different β-nitrostyrenes were synthesized in 55-87% yield after purification. β-nitrostyrenes containing electron-donating groups showed higher yields. The reaction was failed when aliphatic and heteroaromatic nitroalkenes and β-nitrostyrenes with electron-withdrawing substituent were employed. Finally, three plausible mechanistic routes were proposed for the reaction, starting from the nucleophilic addition of triphenylphosphite to α-carbon, nitrogen and oxygen atoms.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"36 9","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139382582","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
MCR-based heteroannulations: A direct access to fused tetrazolo piperazinones and 1,4-diazepanones 基于 MCR 的异annation：直接获得融合的四唑并哌嗪酮和 1,4-二氮杂环庚酮
Synlett Pub Date : 2024-01-05 DOI: 10.1055/a-2239-6897
Constantinos G. Neochoritis, Eirini Fotopoulou, Alexandros Vasilakis
{"title":"MCR-based heteroannulations: A direct access to fused tetrazolo piperazinones and 1,4-diazepanones","authors":"Constantinos G. Neochoritis, Eirini Fotopoulou, Alexandros Vasilakis","doi":"10.1055/a-2239-6897","DOIUrl":"https://doi.org/10.1055/a-2239-6897","url":null,"abstract":"Exploiting the chemistry of bifunctional isocyanides, straightforward, rapid and scalable Ugi-tetrazole-based MCR heteroannulations are described. Our synthetic approach provides a series of diverse fused tetrazolo piperazinones and 1,4-diazepanones in just one step.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"46 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139381718","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
Directing Hydrogen Isotope Exchange with Aryl Carboxylic Acids 引导芳基羧酸的氢同位素交换
Synlett Pub Date : 2024-01-05 DOI: 10.1055/a-2239-6965
R. Mudd, M. Reid, Laura C. Paterson, J. Atzrodt, V. Derdau, William J. Kerr
{"title":"Directing Hydrogen Isotope Exchange with Aryl Carboxylic Acids","authors":"R. Mudd, M. Reid, Laura C. Paterson, J. Atzrodt, V. Derdau, William J. Kerr","doi":"10.1055/a-2239-6965","DOIUrl":"https://doi.org/10.1055/a-2239-6965","url":null,"abstract":"A highly effective and selective ortho-directed hydrogen isotope exchange process for aryl carboxylic acids has been achieved using an iridium(I) N-heterocyclic carbene/phosphine complex under mild and neutral conditions. Good levels of deuterium incorporation have been delivered across a wide array of examples, including within a number of biologically active drug compounds.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"44 9","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139381750","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
Chemical Synthesis and Antitumor Evaluation of Chikusetsusaponin IVa Butyl Ester and Its Analogues Chikusetsusaponin IVa 丁酯及其类似物的化学合成和抗肿瘤评价
Synlett Pub Date : 2024-01-05 DOI: 10.1055/a-2239-6717
Jibin Zheng, Yanxiao Wang, Yiyue Zhang, Jingjing Rong, Dongjuan He, Xiaotong Wang, Liangliang Zhang, Jianguang Xu, Peng Cao, You Yang
{"title":"Chemical Synthesis and Antitumor Evaluation of Chikusetsusaponin IVa Butyl Ester and Its Analogues","authors":"Jibin Zheng, Yanxiao Wang, Yiyue Zhang, Jingjing Rong, Dongjuan He, Xiaotong Wang, Liangliang Zhang, Jianguang Xu, Peng Cao, You Yang","doi":"10.1055/a-2239-6717","DOIUrl":"https://doi.org/10.1055/a-2239-6717","url":null,"abstract":"Chikusetsusaponin IVa butyl ester (CS-IVa-Be) is a triterpene saponin that acts as a novel IL6R antagonist for inducing breast cancer cell apoptosis. However, the structure-activity relationship of this class of saponins remains unclear. Here we report the gram-scale synthesis of CS-IVa-Be and the efficient preparation of its eight analogues. CS-IVa-Be was demonstrated to have significant antitumor activities against MDA-MB-231, HepG2, and A549 cells. When one of the sugar residues at either 3-OH or 28-COOH position of CS-IVa-Be was cleaved, or the length of the alkyl chain on the D-glucuronic acid residue of CS-IVa-Be was changed, these analogues showed varied inhibitory activities against the cancer cell lines. Notably, the carboxylic acid form of CS-IVa-Be exhibited stronger antitumor activity against MDA-MB-231 cells. Furthermore, the carboxylic acid form of CS-IVa-Be inhibited MDA-MB-231 cell proliferation in a dose-dependent manner by arresting cell cycle at the G2/M phase.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"114 16","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139383413","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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