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Preparation of palygorskite grafted fluorescent covalent organic framework and the application in CC coupling reactions 坡缕石接枝荧光共价有机骨架的制备及其在CC偶联反应中的应用
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-12 DOI: 10.1016/j.tetlet.2025.155641
Yun Lei , Xinyu Bai , Shuo Tian , Xin Wang , Huiying Zhan , Haixiong Shi , Penghui Zhang , Shuxia Zhang , Jixia Wang , Xuan Yao , Quanlu Yang , Shang Wu
{"title":"Preparation of palygorskite grafted fluorescent covalent organic framework and the application in CC coupling reactions","authors":"Yun Lei ,&nbsp;Xinyu Bai ,&nbsp;Shuo Tian ,&nbsp;Xin Wang ,&nbsp;Huiying Zhan ,&nbsp;Haixiong Shi ,&nbsp;Penghui Zhang ,&nbsp;Shuxia Zhang ,&nbsp;Jixia Wang ,&nbsp;Xuan Yao ,&nbsp;Quanlu Yang ,&nbsp;Shang Wu","doi":"10.1016/j.tetlet.2025.155641","DOIUrl":"10.1016/j.tetlet.2025.155641","url":null,"abstract":"<div><div>The fluorescent material Pal/COF-SNW is obtained by grafting a fluorescent covalent organic frameworks (COF-SNW) onto the surface of palygorskite with covalent bonds. Pal/COF-SNW shows strong fluorescence in THF solution and achieved effective detection of metal Pd<sup>2+</sup>. Interestingly, the metal palladium attaching to the COF-SNW can be initially determined by the fluorescence change before and after the addition of Pd<sup>2+</sup>, without relying on a series of physical characterization. At the same time, Pal/COF-SNW can also be applied as a good supporter for heterogeneous catalysts. The synthesized Pd-COF-SNW displays an outstanding catalytic activity for Suzuki-Miyaura and Heck coupling reactions in the aqueous phase and obtains the desired products in good to excellent yields, even the partner of coupling reaction is aryl chlorides. It is noteworthy that the catalysts is stable and recycling, it could be used at least seven times continuously without obvious leaching out of the palladium.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155641"},"PeriodicalIF":1.5,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144168438","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
Base-promoted [3+2]-cycloaddition of N-alkoxy-4-oxo-acrylamides with isatins for stereoselective synthesis of spirooxindole-2-oxazolidinones 碱促进的[3+2]n -烷氧基-4-氧丙烯酰胺与isatins的环加成用于立体选择性合成螺氧吲哚-2-恶唑烷酮
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-11 DOI: 10.1016/j.tetlet.2025.155624
Yeongju Kim, Sung-Gon Kim
{"title":"Base-promoted [3+2]-cycloaddition of N-alkoxy-4-oxo-acrylamides with isatins for stereoselective synthesis of spirooxindole-2-oxazolidinones","authors":"Yeongju Kim,&nbsp;Sung-Gon Kim","doi":"10.1016/j.tetlet.2025.155624","DOIUrl":"10.1016/j.tetlet.2025.155624","url":null,"abstract":"<div><div>We have developed a novel base-promoted [3+2]-cycloaddition reaction between <em>N</em>-alkoxy-4-oxo-acrylamides and isatins. This method provides a practical and efficient protocol for synthesizing biologically relevant spirooxindole-2-oxazolidinones under mild conditions. The reaction proceeds with moderate to good yields and diastereoselectivities, showcasing its utility for constructing complex spirooxindole frameworks.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"164 ","pages":"Article 155624"},"PeriodicalIF":1.5,"publicationDate":"2025-05-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143942040","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
Ag-promoted radical decarboxylative annulation of α-keto acids with terminal alkynes to construct Indenones ag促进α-酮酸与末端炔自由基脱羧环构吲哚酮
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-11 DOI: 10.1016/j.tetlet.2025.155648
Hong Dai , Lei Luo , Luo Yang
{"title":"Ag-promoted radical decarboxylative annulation of α-keto acids with terminal alkynes to construct Indenones","authors":"Hong Dai ,&nbsp;Lei Luo ,&nbsp;Luo Yang","doi":"10.1016/j.tetlet.2025.155648","DOIUrl":"10.1016/j.tetlet.2025.155648","url":null,"abstract":"<div><div>An Ag-promoted radical decarboxylative annulation of α-keto acids with terminal alkynes to provide C2 benzoylated indenones is realized, via radical decarboxylation, addition and cyclization cascade. Terminal alkynes were used directly as the substrate with excellent reigo-selectivity. The second benzoyl radical was installed onto the C2 of indeonone, benefiting the potential post-functionalization.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155648"},"PeriodicalIF":1.5,"publicationDate":"2025-05-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143949121","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
Electrocatalytic intramolecular cross-dehydrogenative coupling for synthesis of fused heterocyclic compounds bearing tetrahydroisoquinoline core
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-10 DOI: 10.1016/j.tetlet.2025.155646
Han-ge Li , Yun-fei Liu , Jing-nan Cui , Lei Shi
{"title":"Electrocatalytic intramolecular cross-dehydrogenative coupling for synthesis of fused heterocyclic compounds bearing tetrahydroisoquinoline core","authors":"Han-ge Li ,&nbsp;Yun-fei Liu ,&nbsp;Jing-nan Cui ,&nbsp;Lei Shi","doi":"10.1016/j.tetlet.2025.155646","DOIUrl":"10.1016/j.tetlet.2025.155646","url":null,"abstract":"<div><div>An intramolecular cross-dehydrogenative coupling of N-aryl substituted tetrahydroisoquinolines under electrooxidation condition was developed. The addition of TEMPO and BINOL-derived phosphoric acids allowed the reaction to proceed at low electrode potentials and without the need of additional oxidizers and metals. The corresponding fused heterocyclic products were obtained in good to excellent yields under mild conditions. In addition, the catalysis of chiral 3,3-triazolyl BINOL-derived phosphoric acids enabled this coupling reaction in moderate enantioselectivity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155646"},"PeriodicalIF":1.5,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143943408","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 prenylation of chalcones by a fungal prenyltransferase (AtaPT)
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-10 DOI: 10.1016/j.tetlet.2025.155649
Li Yang , Qianqian Ran , Kang Zhou
{"title":"Regioselective prenylation of chalcones by a fungal prenyltransferase (AtaPT)","authors":"Li Yang ,&nbsp;Qianqian Ran ,&nbsp;Kang Zhou","doi":"10.1016/j.tetlet.2025.155649","DOIUrl":"10.1016/j.tetlet.2025.155649","url":null,"abstract":"<div><div>Prenylation by prenyltransferases exhibits remarkable potential for chalcone modification owing to its high efficiency, specificity, and environmental benignity. The fungal-derived prenyltransferase AtaPT along with prenyl donors of different chain lengths was utilized in this study and five new prenylated chalcones (<strong>1G1</strong>, <strong>1G2</strong>, <strong>2G</strong>, <strong>2D1</strong>, and <strong>2D2</strong>) were chemoenzymatically synthesized. Notably, all prenyl groups were selectively incorporated into ring B of the chalcone scaffold, clearly demonstrating the exquisite regioselectivity of AtaPT. This work not only significantly expands the structural diversity of prenylated chalcones but also provides a biosynthetic module for the green and efficient preparation of prenylated chalcones in synthetic biology.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155649"},"PeriodicalIF":1.5,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143943407","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
Photoinduced decarboxylative carbocation generation from α-amino acid using Selectfluor 用Selectfluor光诱导α-氨基酸脱羧碳正离子生成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-09 DOI: 10.1016/j.tetlet.2025.155642
Mugen Yamawaki , Miwa Ichihashi , Aoi Murakami , Nodoka Maruyama , Seika Kasamatsu , Haruka Fujimoto , Ryoga Hashimoto , Toshiki Furutani , Yasuharu Yoshimi
{"title":"Photoinduced decarboxylative carbocation generation from α-amino acid using Selectfluor","authors":"Mugen Yamawaki ,&nbsp;Miwa Ichihashi ,&nbsp;Aoi Murakami ,&nbsp;Nodoka Maruyama ,&nbsp;Seika Kasamatsu ,&nbsp;Haruka Fujimoto ,&nbsp;Ryoga Hashimoto ,&nbsp;Toshiki Furutani ,&nbsp;Yasuharu Yoshimi","doi":"10.1016/j.tetlet.2025.155642","DOIUrl":"10.1016/j.tetlet.2025.155642","url":null,"abstract":"<div><div>A photoredox system employing 9,10-diphenylanthracene (9,10-DPA) as an electron donor and Selectfluor as both an electron acceptor and oxidant facilitated the conversion of α-amino acids into α-amino alcohols through the formation of carbocations via photoinduced decarboxylation. Various <em>N</em>-protected α-amino acids and dipeptide were successfully converted into their corresponding α-amino alcohols under mild conditions. The reaction proceeded via PET-promoted decarboxylation of <em>N-</em>protected α-amino acids using 9,10-DPA and Selectfluor to generate alkyl radicals that were subsequently oxidized by Selectfluor to form carbocations.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155642"},"PeriodicalIF":1.5,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144240967","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 novel axial chiral benzo[g]quinoline ligand partnered with AgOTf to enantioselectively catalyse a Mannich reaction between isatin N-Boc ketimines and acetylacetone 一种新型轴向手性苯并[g]喹啉配体与AgOTf配合对映选择性催化isatin N-Boc酮胺与乙酰丙酮之间的Mannich反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-08 DOI: 10.1016/j.tetlet.2025.155644
Su-Fan Gao , Qian-Mao Zhang , Guo Cheng , Chun-Chun Tang , Wen-Juan Wan , Li-Xin Wang
{"title":"A novel axial chiral benzo[g]quinoline ligand partnered with AgOTf to enantioselectively catalyse a Mannich reaction between isatin N-Boc ketimines and acetylacetone","authors":"Su-Fan Gao ,&nbsp;Qian-Mao Zhang ,&nbsp;Guo Cheng ,&nbsp;Chun-Chun Tang ,&nbsp;Wen-Juan Wan ,&nbsp;Li-Xin Wang","doi":"10.1016/j.tetlet.2025.155644","DOIUrl":"10.1016/j.tetlet.2025.155644","url":null,"abstract":"<div><div>First example of AgOTf catalysed enantioselective Mannich reaction between isatin N-Boc ketimines and acetylacetone partnered with a novel axial chiral benzo[<em>g</em>]quinoline ligand <strong>B1</strong> has been disclosed. A series of multifunctional chiral 3-substituted 3-amino quaternary oxindoles have been obtained in good enantioselectivities (up to 92:8er) with high yields (61–91 % yields). After a simple recrystallization, the enantioselectivity of almost every chiral product may be greatly improved (up to 99:1er), which provides an alternative method for easy availability of high enantiomeric purity of bioactive chiral 3-substituted 3-amino quaternary oxindoles. This work has successfully demonstrated the good performances of a new kind of axially biaryl quinoline ligands and enriched the application of silver salts in asymmetric catalysis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155644"},"PeriodicalIF":1.5,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144242319","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
Design and application of hydroxyl ionic liquids for the supported synthesis of oligopeptides 负载型寡肽合成羟基离子液体的设计与应用
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-08 DOI: 10.1016/j.tetlet.2025.155645
Hao Ling, Shuaijun Ding, Jinzhe Chen, Zhitian Huang, Jiayi Wang, Yanqing Peng, Gonghua Song
{"title":"Design and application of hydroxyl ionic liquids for the supported synthesis of oligopeptides","authors":"Hao Ling,&nbsp;Shuaijun Ding,&nbsp;Jinzhe Chen,&nbsp;Zhitian Huang,&nbsp;Jiayi Wang,&nbsp;Yanqing Peng,&nbsp;Gonghua Song","doi":"10.1016/j.tetlet.2025.155645","DOIUrl":"10.1016/j.tetlet.2025.155645","url":null,"abstract":"<div><div>A strategy for the rapid and effective supported synthesis of oligopeptides using a novel hydroxyethyl imidazole-type ionic liquid was developed after systematically optimizing the ionic liquid structure depending on the separation and purification efficiency. This method, which incorporates the advantages of both solid- and liquid-phase synthesis, can not only maintain the homogeneous reaction conditions, but also facilitate the purification process with high product yield. The effectiveness of this approach was demonstrated by the successful synthesis of [Leu<sup>5</sup>]-enkephalin and [Met<sup>5</sup>]-enkephalin (yield ≥70 % and purity ≥95 %). The used ionic liquid support can be effectively recycled.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155645"},"PeriodicalIF":1.5,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144242320","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
Diastereoselective synthesis of 5,5-Difluoroisoxazolidine via [3 + 2] cycloaddition between Nitrones and Difluoroacrylates 硝基酮与二氟丙烯酸酯[3 + 2]环加成法非对映选择性合成5,5-二氟异恶唑烷
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-08 DOI: 10.1016/j.tetlet.2025.155647
Miaomiao Zhang , Lingyu Kong , Shengqiang Li, Shang Gao, Xuanyi Li
{"title":"Diastereoselective synthesis of 5,5-Difluoroisoxazolidine via [3 + 2] cycloaddition between Nitrones and Difluoroacrylates","authors":"Miaomiao Zhang ,&nbsp;Lingyu Kong ,&nbsp;Shengqiang Li,&nbsp;Shang Gao,&nbsp;Xuanyi Li","doi":"10.1016/j.tetlet.2025.155647","DOIUrl":"10.1016/j.tetlet.2025.155647","url":null,"abstract":"<div><div>The incorporation of difluoromethylene (CF<sub>2</sub>) group into the backbone of biomolecules is an appealing strategy in the drug development. We describe herein a diastereoselective synthesis of 5,5-difluoroisoxazolidine via dipolar [3 + 2] cycloaddition between nitrones and unsymmetric tetra-substituted difluoroacrylates under catalyst-free conditions. This reaction features mild conditions, moderate to good yield as well as excellent regio- and diastereo-selectivities. DFT calculations showed that a spontaneous inversion of the configuration of nitrogen center was involved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155647"},"PeriodicalIF":1.5,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144242321","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
An efficient synthesis of oxazole-fused 3-Aminopyridin-2(1H)-one heterocycles 恶唑- 3-氨基吡啶-2(1H)- 1杂环的高效合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-07 DOI: 10.1016/j.tetlet.2025.155615
Yunge Yuan , Jiacheng Liu , Fangzhi Huang , Changqing Wei , Wei Zhang
{"title":"An efficient synthesis of oxazole-fused 3-Aminopyridin-2(1H)-one heterocycles","authors":"Yunge Yuan ,&nbsp;Jiacheng Liu ,&nbsp;Fangzhi Huang ,&nbsp;Changqing Wei ,&nbsp;Wei Zhang","doi":"10.1016/j.tetlet.2025.155615","DOIUrl":"10.1016/j.tetlet.2025.155615","url":null,"abstract":"<div><div>3-Aminopyridin-2(1<em>H</em>)-one derivatives are of high interest due to their biological activity, and oxazole-fused heterocyclic compounds are also important pharmacophore in medicinal chemistry. Starting from commercially available materials, this article presents an efficient synthesis of oxazole-fused 3-aminopyridin-2(1<em>H</em>)-one via CuI-catalyzed intramolecular C<img>N coupling. This method has a wide range of substrate adaptability.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"164 ","pages":"Article 155615"},"PeriodicalIF":1.5,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143942038","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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