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Phenanthrolines as Energy Transfer Photocatalysts for the E → Z Isomerization of Alkenes 邻菲罗啉作为烯烃E→Z异构化的能量转移光催化剂
4区 化学
Synthesis-Stuttgart Pub Date : 2024-12-16 DOI: 10.1055/a-2502-8374
Dequn Sun, Kun‐Quan Chen, Xiang-Yu Chen, Xiaobo Chen, Jia Zhang
{"title":"Phenanthrolines as Energy Transfer Photocatalysts for the E → Z Isomerization of Alkenes","authors":"Dequn Sun, Kun‐Quan Chen, Xiang-Yu Chen, Xiaobo Chen, Jia Zhang","doi":"10.1055/a-2502-8374","DOIUrl":"https://doi.org/10.1055/a-2502-8374","url":null,"abstract":"Abstract Phenanthrolines have been widely employed as chelating ligands for transition metals. Herein, this study investigates the utility of substituted o-phenanthrolines as independent photosensitizers for the E → Z isomerization of alkenes. The findings underscore the versatility of o-phenanthrolines, providing a straightforward, metal-free, and cost-effective method for synthesizing Z-alkenes.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 12","pages":"1928-1935"},"PeriodicalIF":0.0,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147900403","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
Consecutive Sonogashira–Suzuki–Michael Cyclization: Three-Component Synthesis of Phenanthridines and Benzo[c]chromenes 连续sonogashura - suzuki - michael环化：三组分合成菲并苯胺[c]
4区 化学
Synthesis-Stuttgart Pub Date : 2024-11-29 DOI: 10.1055/a-2493-3436
Thomas J. J. Müller, G. Hendrik Schmitz, Leonard Karl, Christian Ganter
{"title":"Consecutive Sonogashira–Suzuki–Michael Cyclization: Three-Component Synthesis of Phenanthridines and Benzo[c]chromenes","authors":"Thomas J. J. Müller, G. Hendrik Schmitz, Leonard Karl, Christian Ganter","doi":"10.1055/a-2493-3436","DOIUrl":"https://doi.org/10.1055/a-2493-3436","url":null,"abstract":"Abstract The equistoichiometric three-component reaction of an acid chloride, an alkyne, and an ortho-amino- or ortho-hydroxyphenylboronic ester proceeds smoothly to give phenanthridines or benzo[c]chromenes, respectively, with good to quantitative yields in the sense of a Sonogashira–Suzuki–Michael cyclization sequence. In the coupling of ortho-amidophenylboronates, interestingly, after ring closure a subsequent an acyl migration occurs to give 6-(2-(acyloxy)vinyl)phenanthridines.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 04","pages":"855-875"},"PeriodicalIF":0.0,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147881283","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
A Portal to Highly Valuable Pyridonyl Vinyl Sulfonyl Fluorides and Aliphatic Sulfonyl Fluorides 高价值吡donyl乙烯基磺酰氟化物和脂肪族磺酰氟化物的门户
4区 化学
Synthesis-Stuttgart Pub Date : 2024-11-18 DOI: 10.1055/s-0043-1773500
Hua‐Li Qin, Shan Zeng, Eman Fayad, Ola A. Abu Ali, Bing Sun
{"title":"A Portal to Highly Valuable Pyridonyl Vinyl Sulfonyl Fluorides and Aliphatic Sulfonyl Fluorides","authors":"Hua‐Li Qin, Shan Zeng, Eman Fayad, Ola A. Abu Ali, Bing Sun","doi":"10.1055/s-0043-1773500","DOIUrl":"https://doi.org/10.1055/s-0043-1773500","url":null,"abstract":"Abstract A novel and efficient method for selective Michael addition of 2-pyridones to ethenesulfonyl fluoride (ESF) and 1-bromoethene-1-sulfonyl fluoride (BESF) has been developed for constructing a class of pyridonyl aliphatic sulfonyl fluorides and pyridonyl vinyl sulfonyl fluorides in good to excellent yields. This practical method features easy operation, wide substrate scope, and mild reaction conditions.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 04","pages":"835-845"},"PeriodicalIF":0.0,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147886168","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: 2
Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing. 利用吡咯-吡啶分子编辑实现了康帕那定A的简洁全合成。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2024-01-01 Epub Date: 2023-07-03 DOI: 10.1055/a-2107-5159
Brandon S Martin, Donghui Ma, Takeru Saito, Katelyn S Gallagher, Mingji Dai
{"title":"Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing.","authors":"Brandon S Martin, Donghui Ma, Takeru Saito, Katelyn S Gallagher, Mingji Dai","doi":"10.1055/a-2107-5159","DOIUrl":"10.1055/a-2107-5159","url":null,"abstract":"<p><p><i>Lycopodium</i> alkaloid complanadine A, isolated by Kobayashi et al. in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatment for neurodegenerative disorders and persistent pain management. Herein, we reported a concise synthesis of complanadine A using a pyrrole-to-pyridine molecular editing strategy. The use of a nucleophilic pyrrole as the precursor of the desired pyridine enabled an efficient and one-pot construction of the tetracyclic core skeleton of complanadine A and lycodine. The pyrrole group was then converted to a 3-chloropyridine via the Ciamician-Dennstedt one carbon ring expansion. A subsequent C-H arylation between the 3-chloropyridine and a pyridine <i>N</i>-oxide formed the unsymmetrical dimer, which was then advanced to complanadine A. Overall, from a readily available known compound, total synthesis of complanadine A was achieved in 11 steps. The pyrrole-to-pyridine molecular editing strategy enabled us to significantly enhance the overall synthetic efficiency. Additionally, as demonstrated by a Suzuki-Miyaura cross coupling, the 3-chloropyridine product from the Ciamician-Dennstedt rearrangement is amenable for further derivatization, offering an opportunity for simplified analog synthesis.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"8 1","pages":"107-117"},"PeriodicalIF":2.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11636943/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89430381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
SYNFORM ISSUE 2023/12 Synform issue 2023/12
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/s-0040-1720617
Matteo Zanda
{"title":"SYNFORM ISSUE 2023/12","authors":"Matteo Zanda","doi":"10.1055/s-0040-1720617","DOIUrl":"https://doi.org/10.1055/s-0040-1720617","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"25 9","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134992841","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
Linked PDF of Table of Contents 链接的PDF目录
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/s-0040-1720098
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720098","DOIUrl":"https://doi.org/10.1055/s-0040-1720098","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"25 6","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134992844","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
Regioselective Synthesis of 2,4- and 2,5-disubstituted 1,3-thiazoles from 2-oxo-2-(amino)ethanedithioates via Base Catalysed Cyclization 碱基催化环化2-氧-2-(氨基)乙二硫酸酯合成2,4-和2,5-二取代1,3-噻唑的区域选择性
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/a-2210-6357
Krishna Ravi Singh, C Santhosh, Kalleshappa Sheela, Marilinganadoddi P Sadashiva
{"title":"Regioselective Synthesis of 2,4- and 2,5-disubstituted 1,3-thiazoles from 2-oxo-2-(amino)ethanedithioates via Base Catalysed Cyclization","authors":"Krishna Ravi Singh, C Santhosh, Kalleshappa Sheela, Marilinganadoddi P Sadashiva","doi":"10.1055/a-2210-6357","DOIUrl":"https://doi.org/10.1055/a-2210-6357","url":null,"abstract":"We herein report efficient methods for synthesis of 2,4- and 2,5-disubstituted-1,3-thiazoles 3(a-i) and 5(a-k) by the cyclization of 2-oxo-2-(amino)ethanedithioates with TosMIC and α-haloketones in high yields. The structures 3a and 5a were confirmed based on X-ray crystallographic studies. In addition, investigation of ground state geometry, electronic and molecular structural properties, FMOs, global reactivity descriptors, MEP and NCI analyses predicted to access the information related to the stability, reactivity, and strength of the interactions present in the molecules by quantum chemical calculations. Further, the potency of derivatives tested against the SARS-Cov2 receptor (PDB ID: 7mc6) via molecular docking approach with binding scores of –6.0 to –8.4 kcal/mol.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"38 2","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134993136","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
Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs 5-(三烷基)硅基戊-1-烯-4-炔-3-酮与肼的反应:合成含唑基发光物质的原始途径
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-13 DOI: 10.1055/s-0043-1763601
Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova
{"title":"Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs","authors":"Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova","doi":"10.1055/s-0043-1763601","DOIUrl":"https://doi.org/10.1055/s-0043-1763601","url":null,"abstract":"Abstract On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me3Si, Et3Si, and t-BuMe2Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"40 16","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136282055","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
Synthesis of All Regioisomers of 2-Aryl Azaindole-3-acetic Acid Derivatives 2-芳基氮唑-3-乙酸衍生物所有区域异构体的合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/a-2206-5900
Taewook Kim, Ju Hyeon Park, Cheol Jeong, Eunjoon Park, Jong Mu Kim, You-Jin Kim, Jung-Nyoung Heo, Cheol-Hong Cheon
{"title":"Synthesis of All Regioisomers of 2-Aryl Azaindole-3-acetic Acid Derivatives","authors":"Taewook Kim, Ju Hyeon Park, Cheol Jeong, Eunjoon Park, Jong Mu Kim, You-Jin Kim, Jung-Nyoung Heo, Cheol-Hong Cheon","doi":"10.1055/a-2206-5900","DOIUrl":"https://doi.org/10.1055/a-2206-5900","url":null,"abstract":"A novel protocol was developed for synthesizing 2-aryl substituted azaindole-3-acetic acid derivatives from 2-aminoazacinnamic acid derivatives and aryl aldehydes through an imino-Stetter reaction. Condensation of 2-aminoazacinnamic acid derivatives with aldehydes forms the corresponding aldimines, which are then treated with cyanide to yield the desired 2-aryl substituted azaindole-3-acetic acid derivatives. Notably, this protocol could be employed for the synthesis of all regioisomers of azaindole-3-acetic acid derivatives by using the appropriate azacinnamic acid derivatives.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135392120","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
Synthetic Access to 1,3-Butadiynes via Electro-redox Cuprous Catalyzed Dehydrogenative Csp-Csp Homocoupling of Terminal Acetylenes 电氧化还原亚铜催化末端乙炔脱氢Csp-Csp均偶联制备1,3-丁二炔
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/a-2206-6023
Murugan Krishnan, Kathiresan Murugavel, Chandrasekar Praveen
{"title":"Synthetic Access to 1,3-Butadiynes via Electro-redox Cuprous Catalyzed Dehydrogenative Csp-Csp Homocoupling of Terminal Acetylenes","authors":"Murugan Krishnan, Kathiresan Murugavel, Chandrasekar Praveen","doi":"10.1055/a-2206-6023","DOIUrl":"https://doi.org/10.1055/a-2206-6023","url":null,"abstract":"Herein, we have disclosed the oxidative homocoupling of terminal alkynes under electrochemically generated cuprous catalysis. The scope of this protocol is established by preparing an array of structurally and electronically different 1,3-butadiyne derivatives. Good synthetic yields, functional group tolerance, oxidant-free conditions and no cross-selectivity are some of the intrinsic advantages of this methodology. The developed chemistry features the electro-redox formation of copper-acetylide, an intermediate appropriate for the Csp-Csp coupling step. The chemical state of copper in the acetylide intermediate was found be Cu(I) as confirmed by click-trapping experiments, CV, EPR and XPS. Competition reaction to determine the reactivity of electronically dissimilar acetylenes revealed that the product ratio is rather dependent on the electronic nature of alkynyl substituents. To highlight the synthetic value of the products, selected diynes were subjected to chemical diversification.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"9 10","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135392121","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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