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NCBSI/TEA: A reagent system for rapid and efficient synthesis of isoxazolines from aldoxime
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155489
Nilesh B. Patil , Rhutuja Patil , Ganesh U. Chaturbhuj
{"title":"NCBSI/TEA: A reagent system for rapid and efficient synthesis of isoxazolines from aldoxime","authors":"Nilesh B. Patil ,&nbsp;Rhutuja Patil ,&nbsp;Ganesh U. Chaturbhuj","doi":"10.1016/j.tetlet.2025.155489","DOIUrl":"10.1016/j.tetlet.2025.155489","url":null,"abstract":"<div><div>This report describes an efficient method for synthesizing isoxazolines from aldoximes using NCBSI as a reagent. In this protocol, <em>N</em>-chloro-<em>N</em>-(phenylsulfonyl)benzene sulfonamide (NCBSI) oxidized aldoximes into nitrile oxide. The nitrile oxide underwent 1,3-dipolar cycloaddition to alkenes, giving isoxazolines in good to excellant yields. Furthermore, the precursor <em>N</em>-(phenylsulfonyl)benzene sulfonamide was recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155489"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150503","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
Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155487
Yu Bao, HaiHui Zhu, Hai Huang
{"title":"Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition","authors":"Yu Bao,&nbsp;HaiHui Zhu,&nbsp;Hai Huang","doi":"10.1016/j.tetlet.2025.155487","DOIUrl":"10.1016/j.tetlet.2025.155487","url":null,"abstract":"<div><div>Selective nonclassic propargylic substitutions have been a research focus in recent years. Herein, we developed a tandem γ-selective propargylic substitution and ring closure reaction of vinyl ethynylethylene carbonates (VEECs), efficiently synthesizing a series of 4<em>H</em>-pyran compounds. Additionally, the synthetic applications demonstrated that the products have significant synthetic potential in the synthesis of spirocyclic compounds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155487"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143132699","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
Multifunctional Cys labeling-directed N-terminus-selective stapling strategy development
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-24 DOI: 10.1016/j.tetlet.2025.155480
Yabo Deng , Yisheng Cao , Yi Zhou , Zhiqiang Shen , Danna Chen , Shunqing Wang , Wenjin Yan , Jian Han , Jinqi Huang
{"title":"Multifunctional Cys labeling-directed N-terminus-selective stapling strategy development","authors":"Yabo Deng ,&nbsp;Yisheng Cao ,&nbsp;Yi Zhou ,&nbsp;Zhiqiang Shen ,&nbsp;Danna Chen ,&nbsp;Shunqing Wang ,&nbsp;Wenjin Yan ,&nbsp;Jian Han ,&nbsp;Jinqi Huang","doi":"10.1016/j.tetlet.2025.155480","DOIUrl":"10.1016/j.tetlet.2025.155480","url":null,"abstract":"<div><div>Protein bioconjugation technology integrates the fields of synthetic chemistry and molecular biology, where <em>N</em>-terminal amino groups are increasingly targeted for site-specific modification strategies due to their unique properties. Herein, we report a novel approach to achieve bioconjugation of cysteine and <em>N</em>-terminal amino groups using multifunctional allyl sulfone-activated esters. The experiments were performed in a biocompatible environment (pH 7.4, 10 mM PBS, 37 °C) with universal sequence compatibility for unprotected random peptides of different lengths. Cyclic peptides show desirable late functionalization modifications (including biotin, alkynyl, and PEG et al.).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155480"},"PeriodicalIF":1.5,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150495","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 and stability of N-ε-phospholysine derivatives
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-20 DOI: 10.1016/j.tetlet.2025.155471
Ryanne K. Ballard, Clifford E. Berkman
{"title":"Synthesis and stability of N-ε-phospholysine derivatives","authors":"Ryanne K. Ballard,&nbsp;Clifford E. Berkman","doi":"10.1016/j.tetlet.2025.155471","DOIUrl":"10.1016/j.tetlet.2025.155471","url":null,"abstract":"<div><div><em>N-ε</em>-Phosphorylated lysine (<em>p</em>Lys) residues have been understudied due to their presumed instability to withstand the conventional acidic conditions used in phosphoprotein and phosphopeptide analysis. While some efforts have been made to develop non-hydrolysable <em>p</em>Lys surrogates, less progress has been made on developing methods to prepare authentic <em>p</em>Lys residue and its derivatives. This study provides a synthetic route to <em>N-ε</em>-phosphorylated lysine models and assesses their pH-dependent stability by use of <sup>31</sup>P NMR and HPLC. While the <em>p</em>Lys models expectedly showed instability at lower pH (3.5), they showed unexpected stability in moderately acidic conditions (pH 5.0). In addition, the <em>p</em>Lys models were sufficiently stable when analyzed utilizing HPLC gradients with an acid modifier (0.1 % TFA).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155471"},"PeriodicalIF":1.5,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150497","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
Rapid construction of a diterpene-inspired tetracyclic skeleton bearing bicyclo[3.2.1]octane rings based on desymmetrization of 1,3-diketones
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-19 DOI: 10.1016/j.tetlet.2025.155470
Hidetoshi Kamada, Haruki Mizoguchi, Akira Sakakura
{"title":"Rapid construction of a diterpene-inspired tetracyclic skeleton bearing bicyclo[3.2.1]octane rings based on desymmetrization of 1,3-diketones","authors":"Hidetoshi Kamada,&nbsp;Haruki Mizoguchi,&nbsp;Akira Sakakura","doi":"10.1016/j.tetlet.2025.155470","DOIUrl":"10.1016/j.tetlet.2025.155470","url":null,"abstract":"<div><div>A synthetic methodology for constructing <em>ent</em>-kaurane-like tetracyclic skeletons possessing a bicyclo[3.2.1]octane moiety has been developed by employing a desymmetrizing sequential cyclization strategy. Using a symmetric diketone as a key branching point, the sequence of desymmetric Friedel–Crafts cyclization and Pd-catalyzed intramolecular α-vinylation of ketone allowed us to construct the <em>ent</em>-kaurane-like tetracyclic skeleton from 1,3-cyclohexanedione in four steps. In contrast, reversing the order of the cyclization steps yielded a pseudo-symmetric tetracyclic skeleton, which is also reminiscent of the kaurane framework.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155470"},"PeriodicalIF":1.5,"publicationDate":"2025-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150494","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
Visible-light-promoted trifluoromethylation/arylation of unactivated alkenes with Togni-CF3 for the synthesis of trifluoromethylated pyrrolo[1,2–a]indoles
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-18 DOI: 10.1016/j.tetlet.2025.155468
Hongni Qin , Yong Zhang , Song Sun
{"title":"Visible-light-promoted trifluoromethylation/arylation of unactivated alkenes with Togni-CF3 for the synthesis of trifluoromethylated pyrrolo[1,2–a]indoles","authors":"Hongni Qin ,&nbsp;Yong Zhang ,&nbsp;Song Sun","doi":"10.1016/j.tetlet.2025.155468","DOIUrl":"10.1016/j.tetlet.2025.155468","url":null,"abstract":"<div><div>Herein, we reported a visible-light-promoted trifluoromethylation/arylation of unactivated alkenes with Togni-CF<sub>3</sub>, leading to a series of trifluoromethylated indole-fused heterocycles in moderate to good yields. Mechanically, this reaction initiated by the radical addition of CF<sub>3</sub> radical to the alkene motif, furnishing an alkyl carbon radical, followed by its addition to the aromatic ring, and then rearomatization to afford the trifluoromethylated pyrrolo[1,2–<em>a</em>]indoles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155468"},"PeriodicalIF":1.5,"publicationDate":"2025-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150493","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 “double-locked” fluorescent probe for HClO/H2S detection
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-17 DOI: 10.1016/j.tetlet.2025.155466
Zhengkun Liu , Qianqian Wang , Wenjie Zhang , Wenyang Li , Xinyue Liu , Xiaoqiang Li , Jialong Gou
{"title":"A “double-locked” fluorescent probe for HClO/H2S detection","authors":"Zhengkun Liu ,&nbsp;Qianqian Wang ,&nbsp;Wenjie Zhang ,&nbsp;Wenyang Li ,&nbsp;Xinyue Liu ,&nbsp;Xiaoqiang Li ,&nbsp;Jialong Gou","doi":"10.1016/j.tetlet.2025.155466","DOIUrl":"10.1016/j.tetlet.2025.155466","url":null,"abstract":"<div><div>This study explores the “double-locked” probe strategy for simultaneous detection of oxidative hypochlorous acid (HClO) and reductive hydrogen sulfide (H<sub>2</sub>S). Drawing on our previous work on push–pull electronic structure-based probe <strong>Sa1</strong>, we designed and synthesized a novel double-locked probe, <strong>An1</strong>, for the simultaneous sensing of HClO and H<sub>2</sub>S. Our results demonstrate that <strong>An1</strong> remains fluorescently quenched in the presence of either HClO or H<sub>2</sub>S alone, while displaying robust fluorescence turn-on upon their coexistence. This detection mechanism is well-supported by mass spectrometry analysis. Reaction kinetics studies reveal excellent responsiveness, and selectivity experiments confirm the specific recognition of HClO and H<sub>2</sub>S. Prior to biological applications, the low cytotoxicity of <strong>An1</strong> was validated through MTT assays. Finally, the applicability of <strong>An1</strong> in biological systems was successfully demonstrated in tumor cells and zebrafish models. This work not only validates the potent double-locked detection capability of <strong>An1</strong> with potential clinical implications but also underscores the versatility of the push–pull electronic structure as a generic platform for double-locked probe design.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155466"},"PeriodicalIF":1.5,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150499","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
Silica mediated 1,6-conjugate addition of indoles and other heterocycles to p-quinone methides under solvent free condition
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-15 DOI: 10.1016/j.tetlet.2024.155398
Ramanand Das , Dip Raj Rai , Deepika Kindo , Kimron Protim Phukan , Taraknath Kundu
{"title":"Silica mediated 1,6-conjugate addition of indoles and other heterocycles to p-quinone methides under solvent free condition","authors":"Ramanand Das ,&nbsp;Dip Raj Rai ,&nbsp;Deepika Kindo ,&nbsp;Kimron Protim Phukan ,&nbsp;Taraknath Kundu","doi":"10.1016/j.tetlet.2024.155398","DOIUrl":"10.1016/j.tetlet.2024.155398","url":null,"abstract":"<div><div>Herein, we report an atom economical, operationally simple, solvent and metal-free, green synthetic method for the synthesis of triarylmethanes (TAMs) and indolyl diarylmethanes (IDMs) using commercial silica gel as recyclable solid support reagents through nucleophilic 1,6-conjugate addition of indoles to <em>p</em>-quinone methides (<em>p</em>-QMs). The method doesn’t require any additional catalyst and is compatible with a wide range of combinations of substituted <em>p</em>-QMs with indoles and other heterocycles giving good to excellent yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155398"},"PeriodicalIF":1.5,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143151332","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
Rapid construction of S-containing spirooxindoles and dispirooxindoles via annulation of MBH maleimides of isatins
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-13 DOI: 10.1016/j.tetlet.2025.155452
Kun Huang , Kai-Hua Zhang , Zi-Ying Xiao , Ying Han , Jing Sun , Chao-Guo Yan
{"title":"Rapid construction of S-containing spirooxindoles and dispirooxindoles via annulation of MBH maleimides of isatins","authors":"Kun Huang ,&nbsp;Kai-Hua Zhang ,&nbsp;Zi-Ying Xiao ,&nbsp;Ying Han ,&nbsp;Jing Sun ,&nbsp;Chao-Guo Yan","doi":"10.1016/j.tetlet.2025.155452","DOIUrl":"10.1016/j.tetlet.2025.155452","url":null,"abstract":"<div><div>The novel S-containing spirooxindoles and dispirooxindoles were conveniently synthesized from the annulation reaction of MBH maleimides with S-containing nucleophiles. The annulation reaction of pyridinium 1,4-zwitterionic thiolates and MBH maleimides of isatins in refluxing chloroform afforded functionalized spiro[indoline-3,4′-thiopyrano[2,3-<em>c</em>]pyrroles] in satisfactory yields. On the other hand, DMAP promoted annulation reaction of elemental sulfur and MBH maleimides of isatins in refluxing acetonitrile resulted in functionalized dispiro[indoline-3,8′-thiepino[2,3-<em>c</em>:6,7<em>-c’</em>]dipyrrole-9′,3′’-indolines] in high yields and with high diastereoselectivity. The relative configuration of the dispirooxindoles was confirmed by determining of the single crystal structure.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155452"},"PeriodicalIF":1.5,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143173585","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
Dimroth rearrangements and its applications – Advancements over the past demi-decade
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-10 DOI: 10.1016/j.tetlet.2025.155467
Ani Deepthi, C.B. Meenakshy , Devika Krishnan
{"title":"Dimroth rearrangements and its applications – Advancements over the past demi-decade","authors":"Ani Deepthi,&nbsp;C.B. Meenakshy ,&nbsp;Devika Krishnan","doi":"10.1016/j.tetlet.2025.155467","DOIUrl":"10.1016/j.tetlet.2025.155467","url":null,"abstract":"<div><div>Translocation of heteroatoms in fused ring systems or translocation of exo- or endocyclic heteroatoms in a ring most commonly involves Dimroth rearrangement. The rearrangement is observed commonly in rings containing multiple heteroatoms in presence of acids, bases, heat or light. This review summarizes the reactions involving Dimroth rearrangements reported during the past five years, with mechanistic explanation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155467"},"PeriodicalIF":1.5,"publicationDate":"2025-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150498","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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