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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
Expeditious Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Type 7A 7A型肺炎链球菌荚膜多糖六糖重复单元的快速合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/s-0040-1720095
Samim Sahaji, Pradip Shit, Anup Kumar Misra, Swapan Kumar Jana
{"title":"Expeditious Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Type 7A","authors":"Samim Sahaji, Pradip Shit, Anup Kumar Misra, Swapan Kumar Jana","doi":"10.1055/s-0040-1720095","DOIUrl":"https://doi.org/10.1055/s-0040-1720095","url":null,"abstract":"Abstract The hexasaccharide repeating unit corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 7A has been synthesized in good yield using [3+2+1] block synthetic strategy. The synthetic strategy involved a number of challenging stereoselective glycosylation steps, which include β-selective glycosylation of l-rhamnosyl thioglycoside donor, α-selective glycosylations of 2-azido-2-deoxy-d-glucopyranosyl thioglycoside donor and d-galactopyranosyl donor together with the formation of β-glycoside of d-galactosamine moiety and α-glycoside of l-rhamnosyl moiety. Suitably functionalized thioglycosides have been used as glycosyl donors and a combination of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf­) has been used as glycosylation promoter.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" 6","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135340663","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
Sequential One-Pot Synthesis of β-Amino-γ-keto-malonates from Nitro-Substituted Donor-Acceptor Cyclopropanes 硝基取代给受体环丙烷一锅法合成β-氨基-γ-酮丙二酸酯
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/a-2206-3750
Selvi Subramani, Meenakshi Maniarasu, Visalini Chidambaram, Kannupal Srinivasan
{"title":"Sequential One-Pot Synthesis of β-Amino-γ-keto-malonates from Nitro-Substituted Donor-Acceptor Cyclopropanes","authors":"Selvi Subramani, Meenakshi Maniarasu, Visalini Chidambaram, Kannupal Srinivasan","doi":"10.1055/a-2206-3750","DOIUrl":"https://doi.org/10.1055/a-2206-3750","url":null,"abstract":"A sequential one-pot procedure has been developed for the access of β-Amino-γ-keto-malonates from nitro-substituted donor-acceptor cyclopropanes and four different N-compounds. The reaction proceeds through in situ generation of aroylmethylidenemalonates from the nitro cyclopropanes via Kornblum type ring-opening oxidation using DMSO and subsequent aza-Michael addition with the N-compounds. To prove the synthetic utility of the resulting products, one of them was transformed into a pyridazinone derivative.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"3 18","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135391418","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 Ser-Ala-Ala Cyclic Desmosine Ser-Ala-Ala环氨基葡萄糖的合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-07 DOI: 10.1055/a-2205-7105
Shogo Satoh, Daria Baut, Moena Hirao, Daisuke Watanabe, Rina Suzuki, Toyonori Usuki
{"title":"Synthesis of Ser-Ala-Ala Cyclic Desmosine","authors":"Shogo Satoh, Daria Baut, Moena Hirao, Daisuke Watanabe, Rina Suzuki, Toyonori Usuki","doi":"10.1055/a-2205-7105","DOIUrl":"https://doi.org/10.1055/a-2205-7105","url":null,"abstract":"Elastin is present in the extracellular matrix of various tissues, most abundantly in the aorta and major vascular vessels, and is formed by self-assembly followed by concomitant crosslinkers of tropoelastin, an elastin precursor. Desmosine is a pyridinium-based tetrafunctional amino acid that serves as an important crosslinker to bind the polymeric chains of peptides in the 3D network of elastin. Despite its significance, the detailed structure of elastin has not been elucidated. In this work, we report the synthesis of a cyclic desmosine peptide designed to mimic elastin, which could serve as a compound for mass spectrometric analysis to elucidate crosslinking structures. The synthesis involved stepwise and regioselective palladium-catalyzed cross-couplings, and inter- and intramolecular condensations.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"18 3","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135539780","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
Total Synthesis of the Pyrrole Alkaloids Strychnuxinal and Strychnuxin 吡咯类生物碱士的宁和士的宁的全合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-07 DOI: 10.1055/s-0043-1763603
Keith P. Reber, Neechi F. Okwor, Priyansh D. Gujarati
{"title":"Total Synthesis of the Pyrrole Alkaloids Strychnuxinal and Strychnuxin","authors":"Keith P. Reber, Neechi F. Okwor, Priyansh D. Gujarati","doi":"10.1055/s-0043-1763603","DOIUrl":"https://doi.org/10.1055/s-0043-1763603","url":null,"abstract":"Abstract The first asymmetric total syntheses of the fused-pyrrole alkaloids strychnuxinal and strychnuxin have been achieved in 6 and 7 steps, respectively, starting from commercially available (±)-4-chlorostyrene oxide. Key steps in the synthetic route include a regioselective epoxide opening, a reductive etherification sequence to form the central 1,4-oxazine ring, and a late-stage phenol synthesis using a mild palladium-catalyzed coupling reaction. Notably, the optimized synthetic sequence presented avoids the use of traditional protecting groups. Total synthesis of these two structurally related natural products confirmed both their constitution (via NMR and X-ray crystallography) and their absolute configuration (via optical rotation).","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"39 3","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135432137","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
Metal-Free Synthesis of 9-Sulfenylphenanthrenes via HNO3/HCl Promoted Annulation of 2-Alkynyl Biaryls with Disulfides HNO3/HCl促进2-炔基双芳基与二硫化物环化无金属合成9-亚砜基菲
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-06 DOI: 10.1055/a-2204-8461
Tian Luan, xiaocheng huang, Zhixiang Yao, Hui Su, Wan-Guo Yu
{"title":"Metal-Free Synthesis of 9-Sulfenylphenanthrenes via HNO3/HCl Promoted Annulation of 2-Alkynyl Biaryls with Disulfides","authors":"Tian Luan, xiaocheng huang, Zhixiang Yao, Hui Su, Wan-Guo Yu","doi":"10.1055/a-2204-8461","DOIUrl":"https://doi.org/10.1055/a-2204-8461","url":null,"abstract":"A metal-free thiolative annulation of 2-alkynylbiaryls with disulfides has been developed. This mild and efficient approach was promoted by inexpensive HNO3/HCl and afforded a range of corresponding 9-sulfenylphenanthrenes in good to excellent yields with a broad substrate scope and high functional group tolerance. Both sulfide groups of the disulfide reagent were used in the reaction.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"10 5","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135680017","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
Rhodium(III)-Catalyzed C–H Activation in Indole: A Comprehensive Report (2017–2022) 铑(III)在吲哚中催化C-H活化:综合报告(2017-2022)
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-06 DOI: 10.1055/s-0042-1751497
Biplab Gope, Anupam Mishra, Satish K. Awasthi
{"title":"Rhodium(III)-Catalyzed C–H Activation in Indole: A Comprehensive Report (2017–2022)","authors":"Biplab Gope, Anupam Mishra, Satish K. Awasthi","doi":"10.1055/s-0042-1751497","DOIUrl":"https://doi.org/10.1055/s-0042-1751497","url":null,"abstract":"Abstract In the realm of synthetic organic chemistry, the catalysis of directed C–H activation by transition metals is an outstanding and efficient method for the synthesis of natural products, organic materials, and fundamental organic building blocks. Notably, this strategy has experienced remarkable advances in recent years, particularly in its application to various substrate classes, including the essential indole scaffold. Indole is a highly sought-after target in organic chemistry. The significance of indole extends beyond its use in total synthesis and drug discovery. It also serves as an important tool in the development of pharmaceutical agents, agrochemicals, and materials. By targeting indole, synthetic chemists can access a wide range of bioactive compounds, which opens new avenues for drug development and chemical biology research. The synthesis of structurally varied indoles has been greatly aided by the development of a comprehensive toolkit made possible by the use of C–H activation as a versatile functionalization platform. This review highlights the latest breakthroughs in rhodium-catalyzed C–H activation at the C2, C4, and C7 positions of the indole scaffold. These developments represent significant progress in the field and hold promising potential for further advances in the synthesis of indole-based compounds. 1 Introduction 2 The Development of Rhodium-Catalyzed C–H Activation 3 General Mechanistic Introduction to Rh(III)-Catalyzed C–H Activation 4 Direct C–H Functionalization of Indoles 4.1 C2 Activation of Indoles 4.2 C4 Activation of Indoles 4.3 Dual C–H Activation Strategy 4.4 C7 Activation of Indoles 5 Conclusion","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"6 5","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135584916","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
Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation 膦配体在镍催化烯烃迁移氢烷基化中的作用
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-06 DOI: 10.1055/a-2204-8921
Qing-Wei Zhu, Deguang Liu, Zhen Li, Jia-Wang Wang, Wan Nie, Xi Lu, Yao Fu
{"title":"Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation","authors":"Qing-Wei Zhu, Deguang Liu, Zhen Li, Jia-Wang Wang, Wan Nie, Xi Lu, Yao Fu","doi":"10.1055/a-2204-8921","DOIUrl":"https://doi.org/10.1055/a-2204-8921","url":null,"abstract":"Catalytic alkene hydroalkylation has provided an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation and then cross-coupling mechanism. One of the major tasks in this field is to develop diverse ligands to achieve regioselective control. Herein, we report the investigation of nickel–triphenylphosphine catalyzed remote hydroalkylation of alkenyl amides to access α-branched amines. Various alkenes and alkyl iodides are suitable substrates to deliver desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"11 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135680015","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 formal exchange reaction between ketones and vinyl ethers with solid catalysts 酮和乙烯醚在固体催化剂下的形式交换反应
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-03 DOI: 10.1055/a-2204-2801
Paloma Mingueza-Verdejo, Jose Pedro Cerón-Carrasco, Judit Oliver-Meseguer, Antonio Leyva-Pérez
{"title":"A formal exchange reaction between ketones and vinyl ethers with solid catalysts","authors":"Paloma Mingueza-Verdejo, Jose Pedro Cerón-Carrasco, Judit Oliver-Meseguer, Antonio Leyva-Pérez","doi":"10.1055/a-2204-2801","DOIUrl":"https://doi.org/10.1055/a-2204-2801","url":null,"abstract":"The formal exchange of functional groups in internal positions of two different molecules is of interest in synthetic chemistry, as a simple retrosynthetic strategy. Here we show the formal exchange reaction between internal α–methylene ketones and vinyl ethers, retaining the original C–O bonds. This process offers a new route for the synthesis of vinyl ethers in one step from ketones, including 1,3-diketones, under mild reaction conditions. Besides, the reaction is catalyzed by reusable cheap solids and can be carried out in flow for 20 days without signs of catalyst depletion. Combined experimental and computational mechanistic studies unveil the key role of carbonyl–enol equilibria.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"8 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135872936","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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