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Halogenated Pyridine Derivatives from Cycloaddition / Cycloreversion of Oxazinone and Haloalkyne Precursors. 恶嗪酮和卤代炔前体环加成/环还原的卤代吡啶衍生物。
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-10-30 Epub Date: 2025-08-05 DOI: 10.1016/j.tetlet.2025.155765
Elizabeth A Davis, Megan S Hammett, Jonathan R Scheerer
{"title":"Halogenated Pyridine Derivatives from Cycloaddition / Cycloreversion of Oxazinone and Haloalkyne Precursors.","authors":"Elizabeth A Davis, Megan S Hammett, Jonathan R Scheerer","doi":"10.1016/j.tetlet.2025.155765","DOIUrl":"10.1016/j.tetlet.2025.155765","url":null,"abstract":"<p><p>This study explores the merged cycloaddition/cycloreversion of 1,4-oxazinone substrates with haloalkyne 2π reaction components. Haloalkynes proved generally competent in the Diels-Alder operation and exerted a small influence on the regioselection of the reaction sequence as compared to the reaction sequence with the derived terminal alkyne precursors. Following tandem cycloreversion and elimination of CO<sub>2</sub>, the haloalkynes showed a modest preference for formation of 4-halo pyridine products over 3-halo isomeric variants.</p>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2025-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12373122/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144938095","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
Two novel fungal alkaloids were isolated from Arthrinium malaysianum and their bioactivities 从马来蓟马中分离到两种新的真菌生物碱及其生物活性
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-10-04 DOI: 10.1016/j.tetlet.2025.155841
Jie Zhen Shi , Yan Li Zhang , Jin Hua Yu , Da Mei Wang , Dong Gan , Zhong Tao Ding
{"title":"Two novel fungal alkaloids were isolated from Arthrinium malaysianum and their bioactivities","authors":"Jie Zhen Shi ,&nbsp;Yan Li Zhang ,&nbsp;Jin Hua Yu ,&nbsp;Da Mei Wang ,&nbsp;Dong Gan ,&nbsp;Zhong Tao Ding","doi":"10.1016/j.tetlet.2025.155841","DOIUrl":"10.1016/j.tetlet.2025.155841","url":null,"abstract":"<div><div>Two new fungal alkaloids, arthriniumperazine A (<strong>1</strong>) and arthriniumperazine B (<strong>2</strong>), along with the known mycoediketopiperazine (<strong>3</strong>), were isolated from the endophytic fungus <em>Arthrinium</em> malaysianum DD-1. Notably, this class of fungal alkaloids is scarcely reported, with only compound <strong>3</strong> being previously documented in the literature. The planar structures of <strong>1</strong> and <strong>2</strong> were elucidated through comprehensive spectroscopic analyses, including <sup>1</sup>H/<sup>13</sup>C NMR and HR-ESI-MS. Their absolute configurations were unambiguously determined by comparative ECD calculations. In bioactivity assays, compound <strong>2</strong> exhibited weak α-glucosidase inhibitory activity (18.95 ± 3.77 %, <em>n</em> = 3). For antimicrobial evaluation, compound <strong>1</strong> showed broad-spectrum activity with consistent MICs of 26.60 μg/mL against <em>Bacillus subtilis</em>, <em>Staphylococcus aureus</em>, and <em>Escherichia coli</em>. Compound <strong>2</strong> exhibited selective inhibitory effects against <em>Escherichia coli</em> (26.60 μg/mL) and <em>Staphylococcus aureus</em> (26.60 μg/mL) in the broth microdilution assay, while displaying no significant inhibition against <em>Bacillus subtilis</em>.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155841"},"PeriodicalIF":1.5,"publicationDate":"2025-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145218394","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 synthesis of pyrrolo[2,1-a]isoquinolines through condensation/cycloaddition/aromatization cascade 铜催化缩合/环加成/芳构化级联合成吡咯[2,1-a]异喹啉类化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-10-02 DOI: 10.1016/j.tetlet.2025.155829
Man Jiang , Xue Sheng , Yu Luo, Hai-Lei Cui
{"title":"Copper-catalyzed synthesis of pyrrolo[2,1-a]isoquinolines through condensation/cycloaddition/aromatization cascade","authors":"Man Jiang ,&nbsp;Xue Sheng ,&nbsp;Yu Luo,&nbsp;Hai-Lei Cui","doi":"10.1016/j.tetlet.2025.155829","DOIUrl":"10.1016/j.tetlet.2025.155829","url":null,"abstract":"<div><div>An efficient construction of highly substituted pyrrolo[2,1-<em>a</em>]isoquinoline derivatives has been reached with tetrahydroisoquinolines, aromatic aldehydes and activated olefins through condensation/cycloaddition/aromatization cascade in the presence of copper salts as catalyst. The current approach features the direct use of unactivated aldehydes and high efficiency. Interestingly, the obtained pyrrolo[2,1-<em>a</em>]isoquinolines can be easily modified through reduction, nitration and amidation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155829"},"PeriodicalIF":1.5,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145218396","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
Difluoromethylheteroarylation of unactivated alkenes through remote heteroaryl migration with bis(difluoroacetyl) peroxide 双(二氟乙酰基)过氧化物通过远端异芳基迁移对非活化烯烃的二氟甲基异芳基化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-25 DOI: 10.1016/j.tetlet.2025.155842
Zhiqi Lei , Xiaoyu Wang , Siqi Li , Xia Zhao , Kui Lu
{"title":"Difluoromethylheteroarylation of unactivated alkenes through remote heteroaryl migration with bis(difluoroacetyl) peroxide","authors":"Zhiqi Lei ,&nbsp;Xiaoyu Wang ,&nbsp;Siqi Li ,&nbsp;Xia Zhao ,&nbsp;Kui Lu","doi":"10.1016/j.tetlet.2025.155842","DOIUrl":"10.1016/j.tetlet.2025.155842","url":null,"abstract":"<div><div>We have developed a straightforward method for synthesizing distal difluoromethyl-substituted ketones bearing heteroaryl groups. This approach utilizes difluoromethylheteroarylation of unactivated alkenes through remote heteroaryl migration by employing bis(difluoroacetyl) peroxide (generated in situ from DFAA and urea·H₂O₂) as the difluoromethylating agent. Sunlight was proved to promote this transformation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155842"},"PeriodicalIF":1.5,"publicationDate":"2025-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145218395","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
Electrochemical Di-functionalization: Oxidative Amination and Oxygenation of 4-Hydroxy-α-Benzopyrones under Ring Contraction 电化学双功能化:环收缩下4-羟基-α-苯并吡酮类化合物的氧化胺化和氧化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-24 DOI: 10.1016/j.tetlet.2025.155839
Indrajit Karmakar
{"title":"Electrochemical Di-functionalization: Oxidative Amination and Oxygenation of 4-Hydroxy-α-Benzopyrones under Ring Contraction","authors":"Indrajit Karmakar","doi":"10.1016/j.tetlet.2025.155839","DOIUrl":"10.1016/j.tetlet.2025.155839","url":null,"abstract":"<div><div>We report a catalyst-free, singlet oxygen-mediated electrochemical rearrangement and di-functionalization protocol for the green synthesis of biorelevant 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides from 4-hydroxy-α-benzopyrones. The transformation is carried out using lithium perchlorate as a cost-effective and eco-friendly electrolyte in a 1,4-dioxane:water solvent system at ambient temperature. The proposed mechanism is well supported by systematic control experiments. This one-pot strategy features a broad substrate scope, mild reaction conditions, and delivers good to excellent yields without the need for external catalysts. Key advantages of this method include operational simplicity, environmental sustainability, and high energy efficiency, making it a valuable addition to the toolbox of green synthetic methodologies.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155839"},"PeriodicalIF":1.5,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145218391","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
Transition metal free functionalization of nitrogen heterocycles, triggered and driven by electrophilic acetylenes 亲电乙炔引发和驱动的氮杂环过渡金属游离功能化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-23 DOI: 10.1016/j.tetlet.2025.155837
Boris A. Trofimov, Kseniya V. Belyaeva
{"title":"Transition metal free functionalization of nitrogen heterocycles, triggered and driven by electrophilic acetylenes","authors":"Boris A. Trofimov,&nbsp;Kseniya V. Belyaeva","doi":"10.1016/j.tetlet.2025.155837","DOIUrl":"10.1016/j.tetlet.2025.155837","url":null,"abstract":"<div><div>The review covers the advances reached during the last five years in transition metal free functionalization and modification of nitrogen heterocycles with electrophilic acetylenes. The reactions are triggered and further driven by the initially formed 1,3(4)-dipole complexes (zwitterions), adducts of the nucleophilic attack of nitrogen heterocycles at the triple electrophilic carbon‑carbon bond of the acetylenes. The carbanionic sites of these zwitterions are usually captured by electrophiles such as second molecule of the acetylenes or other electrophilic C<img>C and C<img>O unsaturated compounds, as well as various CH<img>, OH<img>, NH<img>, PH<img> acids thereby raising molecular complexity (in the course of diverse cascade transformations) to a new higher level. The rich energy potential of the activated carbon‑carbon triple bond warrants mild reaction conditions and allows the functionalization to be performed without transition metal catalysts.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155837"},"PeriodicalIF":1.5,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145218393","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 aza-polycyclic aromatic hydrocarbons as organic optoelectronic materials via the Povarov reaction Povarov反应合成氮杂-多环芳烃有机光电材料
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-22 DOI: 10.1016/j.tetlet.2025.155836
Yuanrong Shan , Takaki Kanbara , Junpei Kuwabara
{"title":"Synthesis of aza-polycyclic aromatic hydrocarbons as organic optoelectronic materials via the Povarov reaction","authors":"Yuanrong Shan ,&nbsp;Takaki Kanbara ,&nbsp;Junpei Kuwabara","doi":"10.1016/j.tetlet.2025.155836","DOIUrl":"10.1016/j.tetlet.2025.155836","url":null,"abstract":"<div><div>The Povarov reaction, a classical [4+2] cycloaddition of imines and unsaturated compounds, provides a versatile synthetic platform for the synthesis of nitrogen-doped π-conjugated molecules. This review highlights the recent advances in the application of the Povarov reaction in the synthesis of aza-polycyclic aromatic hydrocarbons (aza-PAHs), which are important components of emerging organic optical and electronic materials. The modularity, one-pot multicomponent compatibility, and broad catalyst scope of the Povarov reaction afford structurally diverse aza-PAHs. Representative examples spanning small molecules, conjugated polymers, covalent organic frameworks (COFs), and molecular cages are discussed, with particular emphasis on their functional properties, including photoluminescence, sensing, circularly polarized luminescence, hole-blocking, and electron transport properties in organic light-emitting diodes. Mechanistic insights into regioselectivity and π-extension are also reviewed to facilitate the future design of aza-PAHs. The Povarov reaction is a powerful synthetic tool for the development of advanced aza-PAH-based materials for optical and electronic applications.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155836"},"PeriodicalIF":1.5,"publicationDate":"2025-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145218392","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-Induced Regioselective Benzylic CH Oxidation of Substituted 6-Aryl-7,8,9,10-tetrahydrobenzo[c]phenanthridine 可见光诱导取代6-芳基-7,8,9,10-四氢苯并[c]菲蒽啶的区域选择性苄基CH氧化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-21 DOI: 10.1016/j.tetlet.2025.155828
Mukesh Kumar , Musfika Khatun , Simra Faraz , Satyajit Singh , Abu Taleb Khan
{"title":"Visible-Light-Induced Regioselective Benzylic CH Oxidation of Substituted 6-Aryl-7,8,9,10-tetrahydrobenzo[c]phenanthridine","authors":"Mukesh Kumar ,&nbsp;Musfika Khatun ,&nbsp;Simra Faraz ,&nbsp;Satyajit Singh ,&nbsp;Abu Taleb Khan","doi":"10.1016/j.tetlet.2025.155828","DOIUrl":"10.1016/j.tetlet.2025.155828","url":null,"abstract":"<div><div>A practical and sustainable protocol for the photocatalytic oxidation of benzylic C<img>H bonds, particularly within polycyclic heteroaromatic (PHA) frameworks, has been developed. In contrast to many previously reported systems, which often rely on long reaction times, narrow-spectrum LEDs, additives, or specialized photoreactors or setups, this method employs inexpensive eosin Y under white LED illumination with molecular oxygen supplied via a balloon. The transformation proceeds under mild conditions without the need for transition metals, hazardous oxidants, or auxiliary additives, and operates via a radical mechanism supported by inhibition studies. The broad substrate tolerance and operational simplicity of this protocol facilitate efficient access to benzylic ketones. Its utility is exemplified in the synthesis of a variety of 6-aryl-8,9-dihydrobenzo[<em>c</em>]phenanthridin-10(7<em>H</em>)-one derivatives, where the substituent at the 6-position plays a critical role in determining product outcome. This method represents one of the few reported examples of late-stage C<img>H functionalization in PHAs under photocatalytic conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155828"},"PeriodicalIF":1.5,"publicationDate":"2025-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145118043","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
Silver-catalyzed regioselective synthesis of benzo[2,7] naphthyridines using ortho-alkynyl quinoline carbaldehyde and anthranilic acid derivatives 银催化邻炔基喹啉乙醛和邻氨基苯甲酸衍生物的区域选择性合成苯并[2,7]萘啶
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-20 DOI: 10.1016/j.tetlet.2025.155835
Kapil Chahal , Ravikumar Badhavath , K. Velangini Sunidhi Reddy , Kirti Vashishtha , K. Rajender Reddy
{"title":"Silver-catalyzed regioselective synthesis of benzo[2,7] naphthyridines using ortho-alkynyl quinoline carbaldehyde and anthranilic acid derivatives","authors":"Kapil Chahal ,&nbsp;Ravikumar Badhavath ,&nbsp;K. Velangini Sunidhi Reddy ,&nbsp;Kirti Vashishtha ,&nbsp;K. Rajender Reddy","doi":"10.1016/j.tetlet.2025.155835","DOIUrl":"10.1016/j.tetlet.2025.155835","url":null,"abstract":"<div><div>This method represents a significant advancement in the synthesis of Benzo[2,7]naphthyridines. The silver-catalyzed cyclization of <em>ortho</em>-alkynyl aldehydes and anthranilic acids proceeds under mild conditions with minimal catalyst loading, providing high yields and excellent regioselectivity. Control experiments and deuteration studies were performed to evaluate the reaction mechanism. The broad substrate scope and scalability make this protocol especially valuable for synthesizing diverse 2,7-naphthyridine derivatives, which are important scaffolds in medicinal chemistry and materials science.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155835"},"PeriodicalIF":1.5,"publicationDate":"2025-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145128258","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
Phosphoric acid-catalyzed regioselective amidation of para-quinone methides with acetonitrile 磷酸催化对醌与乙腈的区域选择性酰胺化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-20 DOI: 10.1016/j.tetlet.2025.155834
Xiu Liu , Hongjun Chen , Chenzhong Jin , Longzhi Zhu , Biquan Xiong
{"title":"Phosphoric acid-catalyzed regioselective amidation of para-quinone methides with acetonitrile","authors":"Xiu Liu ,&nbsp;Hongjun Chen ,&nbsp;Chenzhong Jin ,&nbsp;Longzhi Zhu ,&nbsp;Biquan Xiong","doi":"10.1016/j.tetlet.2025.155834","DOIUrl":"10.1016/j.tetlet.2025.155834","url":null,"abstract":"<div><div>An efficient and atom-economical phosphoric acid-catalyzed amidation of <em>para</em>-quinone methides (<em>p</em>-QMs) with acetonitrile has been developed under mild conditions. Water serves as the sole source of both hydrogen and oxygen atoms, enabling 100 % atom economy in amide bond formation. The reaction exhibits excellent generality across a broad spectrum of electronically and sterically diverse <em>p</em>-QMs, facilitating efficient and highly regioselective synthesis of synthetically valuable <em>N</em>-diarylmethyl-substituted acetamides in good to excellent yields. Step-by-step control experiments and competitive deuterium-labeling KIE studies elucidated the reaction pathway and led to a plausible mechanism based on cumulative experimental evidences.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155834"},"PeriodicalIF":1.5,"publicationDate":"2025-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145157569","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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