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Synthesis of Rhamnose‐Modified Lewis‐X‐Containing Saponins 鼠李糖修饰Lewis - X -含皂苷的合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-28 DOI: 10.1002/ejoc.202500285
Oscar Javier Gamboa Marin, Nitish Verma, Maude Cloutier, Charles Gauthier
{"title":"Synthesis of Rhamnose‐Modified Lewis‐X‐Containing Saponins","authors":"Oscar Javier Gamboa Marin, Nitish Verma, Maude Cloutier, Charles Gauthier","doi":"10.1002/ejoc.202500285","DOIUrl":"https://doi.org/10.1002/ejoc.202500285","url":null,"abstract":"We report the synthesis of betulinic acid and echinocystic acid saponins featuring an unnatural analogue of the Lewis‐X trisaccharide, in which the l‐fucose residue is replaced by l‐rhamnose. These triterpenoid saponins were designed as negative controls for dendritic cell‐specific intercellular adhesion molecule‐3‐grabbing non‐integrin (DC‐SIGN)‐targeted antiviral and immunological studies. The target saponins were synthesized using both iterative and convergent strategies, requiring nine and six steps, respectively, for the longest linear sequence starting from allyl betulinate and allyl echinocystate. Glycosylation reactions were performed using trihalogenoacetimidate and thioglycoside donors, which provided excellent yields and complete control over stereoselectivity. This work establishes a robust foundation for the synthesis of lupane‐ and oleanane‐type triterpenoid saponins incorporating Lewis‐X trisaccharide analogues.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143880482","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Front Cover: Full-Color Fluorescence Solvatochromism of Push-Pull Type Indenoindene Derivatives (Eur. J. Org. Chem. 16/2025) 封面：推拉型茚三酮衍生物的全彩荧光溶剂变色。j . Org。化学16/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-28 DOI: 10.1002/ejoc.202581601
Wakana Kanezaki, Ryutaro Ishikawa, Hayato Tsuji
{"title":"Front Cover: Full-Color Fluorescence Solvatochromism of Push-Pull Type Indenoindene Derivatives (Eur. J. Org. Chem. 16/2025)","authors":"Wakana Kanezaki,&nbsp;Ryutaro Ishikawa,&nbsp;Hayato Tsuji","doi":"10.1002/ejoc.202581601","DOIUrl":"https://doi.org/10.1002/ejoc.202581601","url":null,"abstract":"<p><b>The Front Cover</b> shows how full-color solvatochromic fluorescence has been achieved by using a push–pull type π-conjugated molecule (placed in the flask) featuring a rigid, planar indenoindene core as the fluorophore. The fluorescence quantum yield exceeds 0.90 in aprotic solvents, and the emission color ranges from blue to red depending on solvent polarity, as represented by the colored smoke in the flask. More information can be found in the Research Article by H. Tsuji and co-workers (DOI: 10.1002/ejoc.202401471).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202581601","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143879767","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Metal–Ligand Cooperation for Iron(II)‐Catalyzed Direct Wittig‐Type Olefination from Alcohols in Air 铁（II）催化醇在空气中直接Wittig型烯烃的金属配体配合
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-26 DOI: 10.1002/ejoc.202500257
Subhankar Khanra, Subhangi Saha, Sutanuva Mandal, Nanda Dulal Paul
{"title":"Metal–Ligand Cooperation for Iron(II)‐Catalyzed Direct Wittig‐Type Olefination from Alcohols in Air","authors":"Subhankar Khanra, Subhangi Saha, Sutanuva Mandal, Nanda Dulal Paul","doi":"10.1002/ejoc.202500257","DOIUrl":"https://doi.org/10.1002/ejoc.202500257","url":null,"abstract":"An iron‐catalyzed one‐pot tandem in situ oxidation–Wittig reaction is reported for the synthesis of alkenes. Using a bench‐stable Fe(II) catalyst with a redox‐noninnocent 2‐((4‐chlorophenyl)diazenyl)‐1,10‐phenanthroline ligand scaffold, a broad spectrum of substituted E olefins were synthesized in good yields by the reaction of alcohols with phosphorus ylides. Control reactions and spectroscopic studies indicate synergistic participation of the ligand, which acts as a reservoir of electrons and hydrogen, during the dehydrogenative coupling of alcohols with the phosphorus ylides.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"45 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143875752","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Electrochemically promoted amination of pyrido[2,3-d]pyrimidin-7-ones: efficient synthesis of palbociclib derivatives 电化学促进吡啶[2,3-d]嘧啶-7- 1胺化：帕博西尼衍生物的高效合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1002/ejoc.202500259
Dong Wang, Lixi Zhang, Jiabin Shen, Pengfei Zhang, Chao Shen, Qing Zhu
{"title":"Electrochemically promoted amination of pyrido[2,3-d]pyrimidin-7-ones: efficient synthesis of palbociclib derivatives","authors":"Dong Wang, Lixi Zhang, Jiabin Shen, Pengfei Zhang, Chao Shen, Qing Zhu","doi":"10.1002/ejoc.202500259","DOIUrl":"https://doi.org/10.1002/ejoc.202500259","url":null,"abstract":"The pyrido[2,3-d]-pyrimidin-7-one template is a crucial molecular fragment in antineoplastic drug palbociclib. Considering the importance of pyrido[2,3-d]-pyrimidin-7-one template, herein, we report a simple and environmentally friendly electrocatalytic amination of pyrido[2,3-d]pyrimidin-7-ones with N,N-dialkyl formamides as the amine source and NaBr as the electrolyte. This straightforward and operationally simple protocol opens a green and efficient strategy for the synthesis of palbociclib derivatives in moderate to good yields.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143878046","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
NNN Palladium(II)-Pincer Complex in a Borrowing Hydrogen Process: Alkylation of Indoles NNN钯(II)-钳形配合物的借氢过程：吲哚的烷基化
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1002/ejoc.202500313
Shivkanya Madhavrao Bhujbal, Aabid Abdullah Wani, Prasad V. Bharatam
{"title":"NNN Palladium(II)-Pincer Complex in a Borrowing Hydrogen Process: Alkylation of Indoles","authors":"Shivkanya Madhavrao Bhujbal, Aabid Abdullah Wani, Prasad V. Bharatam","doi":"10.1002/ejoc.202500313","DOIUrl":"https://doi.org/10.1002/ejoc.202500313","url":null,"abstract":"Recently, an azine NNN-Pd(II) non-palindromic pincer complex was generated, and its application in acceptorless dehydrogenative coupling (ADC) was explored. This article establishes the application of the same pincer complex in the borrowing hydrogen process (BHP). Herein, we report the selective synthesis of C-3 alkylated indoles (CAIs). Remarkably, this catalyst enables bis(indolyl)methanes (BIMs) synthesis by tuning the reaction conditions from the same substrates. The control experiments and quantum chemical analysis suggest that C-3 functionalization of indole involves a “Borrowing Hydrogen Process.’’ The formation of BIMs is an additional advantage.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"34 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872743","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Chemoselective thioamidation of potassium acyltrifluoroborates (KATs) and amines using elemental sulfur in aqueous solution 在水溶液中使用单质硫对酰基三氟硼酸钾（KATs）和胺进行化学选择性硫胺化
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1002/ejoc.202500330
Yuanhang Li, Hafiza Zara Tariq, Silong Xu, Jing Li
{"title":"Chemoselective thioamidation of potassium acyltrifluoroborates (KATs) and amines using elemental sulfur in aqueous solution","authors":"Yuanhang Li, Hafiza Zara Tariq, Silong Xu, Jing Li","doi":"10.1002/ejoc.202500330","DOIUrl":"https://doi.org/10.1002/ejoc.202500330","url":null,"abstract":"Bioisosteres serve as valuable design elements for medicinal chemists, enabling the adjustment of the structural and pharmacokinetic properties of bioactive compounds to develop viable drug candidates. Thioamides hold promise as bioisosteres for the commonly used amide pharmacophores. This paper presents a synthesis method for thioamides, achieved through the reaction of potassium acyltrifluoroborates with amines in the presence of elemental sulfur in aqueous solution. The process is simple, mild, and accommodates various polar functional groups, making it ideal for creating amide and thioamide drug libraries. Furthermore, we have synthesized seven bioactive thioamides and their corresponding marketed drug analogs using present method.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867057","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Photoinduced Reaction of Diiodoperfluoroalkanes with Aromatic Compounds: Divergent Synthesis of Two Product Types 二碘全氟烷烃与芳香族化合物的光诱导反应：两种产物类型的发散合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1002/ejoc.202500295
Airi Yamaguchi, Tamako Nakamura, Haruko Shibata, Tadashi Kanbara, Tomoko Yajima
{"title":"Photoinduced Reaction of Diiodoperfluoroalkanes with Aromatic Compounds: Divergent Synthesis of Two Product Types","authors":"Airi Yamaguchi, Tamako Nakamura, Haruko Shibata, Tadashi Kanbara, Tomoko Yajima","doi":"10.1002/ejoc.202500295","DOIUrl":"https://doi.org/10.1002/ejoc.202500295","url":null,"abstract":"Both UV-light-promoted and organic-dye-catalyzed visible-light-promoted reactions of diiodoperfluoroalkanes with an iodine substituent at both ends and substituted anilines were attempted. In the reactions with 1,6- and 1,8-diiodoperfluoroalkanes in the presence of an excess amount of aniline, both ends of the iodide reacted to give a diamine, and the reaction with an excess amount of diiodide gave a monoiodide, in which one end of the diiodide had reacted with the aniline. In contrast, in the case of the 1,4-diiodoperfluoroalkane, the UV reaction yielded cyclization products in which both ends of the diiodine had reacted with the same aromatic ring, while the visible-light reaction yielded products in which only one end had reacted. Since synthetic examples of such cyclization products are limited, we tried the reaction with various aromatic compounds and showed that it is effective for electron-rich aromatic rings. We also discuss the mechanism of these reactions and point out the importance of the redox potential of the iodides.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867122","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Base-Promoted [4+3] Annulation Reaction of Indole-2-carboxamides with β-CF3-1,3-Enynes: Access to Fluorine-Containing Indole-1,2-Fused 1,4-Diazepinones 吲哚-2-羧酰胺与β- cf3 -1,3-炔的碱促进[4+3]环化反应：含氟吲哚-1,2-熔合1,4-二氮平酮的获得
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1002/ejoc.202500323
Lushuang Guo, Chao Pi, Yangjie Wu, Xiuling Cui
{"title":"Base-Promoted [4+3] Annulation Reaction of Indole-2-carboxamides with β-CF3-1,3-Enynes: Access to Fluorine-Containing Indole-1,2-Fused 1,4-Diazepinones","authors":"Lushuang Guo, Chao Pi, Yangjie Wu, Xiuling Cui","doi":"10.1002/ejoc.202500323","DOIUrl":"https://doi.org/10.1002/ejoc.202500323","url":null,"abstract":"An efficient base-promoted approach for the synthesis of fluorine-containing indole-1,2-fused 1,4-diazepinones via [4+3] annulation of indoles with β-CF3-1,3-enynes is presented. This strategy delivers the target products in good to excellent yields under the mild reaction conditions, showcasing high step economy and broad substrate scope. This reaction could be scalable to gram and amenable to diverse functionalization, underscoring its potential utility in pharmaceutical development and materials science.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"129 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872744","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Addressing Synthetic Complexity in Conjugated Polymers: New Synthetic Methods for the Acceptor Units 2,1,3‐benzothiadiazole, 2,3‐dihexylquinoxaline, and 2H‐benzotriazole 解决共轭聚合物合成的复杂性：受体单元2,1,3‐苯并噻唑、2,3‐二己基喹啉和2H‐苯并三唑的新合成方法
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1002/ejoc.202500379
Wyatt D. Wilcox, Hunter V. Hanson, Maxwell Bultman, Seth C. Rasmussen
{"title":"Addressing Synthetic Complexity in Conjugated Polymers: New Synthetic Methods for the Acceptor Units 2,1,3‐benzothiadiazole, 2,3‐dihexylquinoxaline, and 2H‐benzotriazole","authors":"Wyatt D. Wilcox, Hunter V. Hanson, Maxwell Bultman, Seth C. Rasmussen","doi":"10.1002/ejoc.202500379","DOIUrl":"https://doi.org/10.1002/ejoc.202500379","url":null,"abstract":"In an attempt to address the growing problem of synthetic complexity in conjugated organic polymers, the synthesis of the common acceptor units 2,1,3‐benzothiadiazole (BTD), quinoxaline (Qx), and 2H‐benzotriazole (BTA) have been revisited, along with their dibromo derivatives necessary for use in catalytic cross‐coupling. In addition to reducing the total number of synthetic steps, efforts have been made to reduce hazardous reagents and simplify purification. Synthetic complexity index values for both established and newly reported methods are then generated in order to provide a qualitative evaluation of the reduced contribution of these common building blocks to the synthetic complexity of all materials that contain them.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"42 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872749","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Full‐Color Fluorescence Solvatochromism of Push‐Pull Type Indenoindene Derivatives 推拉式茚衍生物的全色荧光溶色性
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401471
Wakana Kanezaki , Ryutaro Ishikawa , Hayato Tsuji
{"title":"Full‐Color Fluorescence Solvatochromism of Push‐Pull Type Indenoindene Derivatives","authors":"Wakana Kanezaki ,&nbsp;Ryutaro Ishikawa ,&nbsp;Hayato Tsuji","doi":"10.1002/ejoc.202401471","DOIUrl":"10.1002/ejoc.202401471","url":null,"abstract":"<div><div>Full‐color fluorescence solvatochromism was demonstrated using two carbon‐bridged oligo(phenylenevinylene) (COPV) derivatives <strong>Ph<sub>2</sub>N‐COPV1(Bu)‐COCH<sub>3</sub></strong> and <strong>[Ph<sub>2</sub>N‐COPV1(Bu)]<sub>2</sub>CO</strong> with a push–pull system, where the donor and acceptor moieties are diphenylamino and a carbonyl group, respectively. In non‐polar cyclohexane, the molecules exhibited blue photoluminescence (λ<sub>PL</sub>=443 and 464 nm) with a locally excited character, while in polar solvents, a charge‐transfer character emerged. In methanol, red emission was observed (λ<sub>PL</sub>=602 and 572 nm). The difference in luminescence maxima between cyclohexane and methanol corresponds to 0.74 and 0.59 eV for <strong>Ph<sub>2</sub>N‐COPV1(Bu)‐COCH<sub>3</sub></strong> and <strong>[Ph<sub>2</sub>N‐COPV1(Bu)]<sub>2</sub>CO</strong>, respectively, which are larger than those of previously reported push–pull systems. The photoluminescence quantum yields of <strong>Ph<sub>2</sub>N‐COPV1(Bu)‐COCH<sub>3</sub></strong> in aprotic solvents were 0.90 and higher regardless of solvent polarity, while they decreased in protic solvents. The molecules also display high extinction coefficients of up to 2.8x10<sup>4</sup> and 6.4x10<sup>4</sup> M<sup>−1</sup> cm<sup>−1</sup>. These data demonstrate the effectiveness of the use of structurally rigid planar COPV framework. Furthermore, <strong>[Ph<sub>2</sub>N‐COPV1(Bu)]<sub>2</sub>CO</strong> showed significant responses to water content in tetrahydrofuran‐water mixed solvents, which highlights its potential for sensing applications.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202401471"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143418430","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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