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Visible-light-induced cycloisomerization of O-tethered 1,6-enynes to phosphinylated 3,6-dihydropyrans 可见光诱导的o系1,6-炔环异构化成膦化3,6-二氢吡喃
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-03 DOI: 10.1016/j.tetlet.2025.155628
Yifan Hu, Silong Chen, Nan Huang, Qian Chen
{"title":"Visible-light-induced cycloisomerization of O-tethered 1,6-enynes to phosphinylated 3,6-dihydropyrans","authors":"Yifan Hu,&nbsp;Silong Chen,&nbsp;Nan Huang,&nbsp;Qian Chen","doi":"10.1016/j.tetlet.2025.155628","DOIUrl":"10.1016/j.tetlet.2025.155628","url":null,"abstract":"<div><div>Phosphorus-substituted heterocycles are core motifs in a large amount of biologically active compounds. In this research, a photocatalytic cycloisomerization of <em>O</em>-tethered 1,6-enynes with diarylphosphine oxides under a visible-light irradiation has been achieved. This method provides rapid and efficient access to phosphinylated heterocycles (27 examples) with good functional group compatibility under mild conditions. Spectroscopic studies suggest that a reductive quenching of the excited photocatalyst Ir(III)* with diarylphosphine oxides generates phosphinyl radicals, which undergo a tandem radical cyclization of <em>O</em>-tethered 1,6-enynes to afford the desired phosphinylated 3,6-dihydropyrans.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155628"},"PeriodicalIF":1.5,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917581","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
Erratum to “Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids” [Tetrahedron Lett. 159 (2025) 155507] 对“对Seebach-Beckwith脱氢丙氨酸的金属和有机催化脱羧自由基加成对光学纯非天然氨基酸的研究和优化”的更正[Tetrahedron Lett] . 159 (2025) 155507]
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-02 DOI: 10.1016/j.tetlet.2025.155616
Ilia Perov, Karizza F. Catenza, Jose Jr Abucay, Yu-Ting Hsiao, John C. Vederas
{"title":"Erratum to “Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids” [Tetrahedron Lett. 159 (2025) 155507]","authors":"Ilia Perov,&nbsp;Karizza F. Catenza,&nbsp;Jose Jr Abucay,&nbsp;Yu-Ting Hsiao,&nbsp;John C. Vederas","doi":"10.1016/j.tetlet.2025.155616","DOIUrl":"10.1016/j.tetlet.2025.155616","url":null,"abstract":"","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155616"},"PeriodicalIF":1.5,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917685","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
Concise synthesis of (±)-gomadalactone A （±）-戈马达拉内酯A的简明合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-29 DOI: 10.1016/j.tetlet.2025.155623
Ryosuke Ashizaki, Ryo Katsuta, Shinnosuke Wakamori, Tomoo Nukada, Ken Ishigami
{"title":"Concise synthesis of (±)-gomadalactone A","authors":"Ryosuke Ashizaki,&nbsp;Ryo Katsuta,&nbsp;Shinnosuke Wakamori,&nbsp;Tomoo Nukada,&nbsp;Ken Ishigami","doi":"10.1016/j.tetlet.2025.155623","DOIUrl":"10.1016/j.tetlet.2025.155623","url":null,"abstract":"<div><div>We report the synthesis of (±)-gomadalactone A, a contact sex pheromone of the white-spotted longicorn beetle (<em>Anoplophora malasiaca</em>). The synthesis employs Vassilikogiannakis' one-pot, photo-driven cyclopentenone synthesis from a furan derivative, followed by lactonization, to efficiently construct a distinctive 3-oxabicyclo[3.3.0]octane framework. This eleven-step process starts from methyl 2-furylacetate, produced (±)-gomadalactone A in an overall yield of 1 %.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155623"},"PeriodicalIF":1.5,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917580","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 direct decarboxylative CH functionalization of azauracils with aliphatic carboxylic acids 银催化的杜鹃酸与脂肪羧酸直接脱羧甲基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-23 DOI: 10.1016/j.tetlet.2025.155619
Jie Zeng , Houwen Zhou , Shenghao Wang , Fenghua Zhang , Fei Li , Jingjing Wang , Lin Li , Tianbao Dong , Mingyue Cui , Feng Li
{"title":"Silver-catalyzed direct decarboxylative CH functionalization of azauracils with aliphatic carboxylic acids","authors":"Jie Zeng ,&nbsp;Houwen Zhou ,&nbsp;Shenghao Wang ,&nbsp;Fenghua Zhang ,&nbsp;Fei Li ,&nbsp;Jingjing Wang ,&nbsp;Lin Li ,&nbsp;Tianbao Dong ,&nbsp;Mingyue Cui ,&nbsp;Feng Li","doi":"10.1016/j.tetlet.2025.155619","DOIUrl":"10.1016/j.tetlet.2025.155619","url":null,"abstract":"<div><div>We propose a novel method for the C<img>H alkylation of azauracils using aliphatic carboxylic acids as alkyl radical precursors, catalyzed by silver. This technique marks a substantial progress in organic synthesis, providing a flexible and effective route for azauracils modification. The method has been successfully applied to a diverse array of primary, secondary and tertiary carboxylic acids, highlighting its broad utility and reliability. The applicability of this method allows the preparation of a range of alkylated azauracil derivatives, which are potential intermediates for the creation of new pharmaceuticals, agrochemicals, and materials.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155619"},"PeriodicalIF":1.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143878759","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
Erratum to ‘Mechanosynthesis of polysubstituted pyridines via FeBr3-catalyzed cascade reaction of arylidene isoxazolones with β-carbonyl esters’ [Tetrahedron Lett. 161 (2025) 155569] “二甲苯催化芳基异恶唑酮与β-羰基酯级联反应的机械合成多取代吡啶”[j] .四面体学报，161(2025):155569。
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-23 DOI: 10.1016/j.tetlet.2025.155607
Lei Wang, Ming-Jun Li, Qing-Hai Li, Peng Xu, Si-Qi Chen, Hui Xu, Ze Zhang
{"title":"Erratum to ‘Mechanosynthesis of polysubstituted pyridines via FeBr3-catalyzed cascade reaction of arylidene isoxazolones with β-carbonyl esters’ [Tetrahedron Lett. 161 (2025) 155569]","authors":"Lei Wang,&nbsp;Ming-Jun Li,&nbsp;Qing-Hai Li,&nbsp;Peng Xu,&nbsp;Si-Qi Chen,&nbsp;Hui Xu,&nbsp;Ze Zhang","doi":"10.1016/j.tetlet.2025.155607","DOIUrl":"10.1016/j.tetlet.2025.155607","url":null,"abstract":"","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155607"},"PeriodicalIF":1.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917684","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
Innovative advancements in transition metal-catalyzed C(sp2)-H bond activation of phthalazinone: Unlocking the gateway to diverse hybrid polyheterocyclic architectures 过渡金属催化邻苯二嗪酮C(sp2)-H键活化的创新进展：打开多种杂化多杂环结构的大门
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-23 DOI: 10.1016/j.tetlet.2025.155618
Swarnali Ghosh , Anindita Sarkar , Rahul Dev Mandal , Asish R. Das
{"title":"Innovative advancements in transition metal-catalyzed C(sp2)-H bond activation of phthalazinone: Unlocking the gateway to diverse hybrid polyheterocyclic architectures","authors":"Swarnali Ghosh ,&nbsp;Anindita Sarkar ,&nbsp;Rahul Dev Mandal ,&nbsp;Asish R. Das","doi":"10.1016/j.tetlet.2025.155618","DOIUrl":"10.1016/j.tetlet.2025.155618","url":null,"abstract":"<div><div>Phthalazinones, a fused diaza heterocycles have been recognized as remarkable structural leads in medicinal chemistry owing to its wider application in pharmaceutical and agrochemical industries. Moreover, having unique structural feature and potent biological activities, this scaffold allures the attention of synthetic chemists toward selective activation and functionalization of C<img>H bonds to synthesize its fused polycyclic frameworks. To attain this goal, transition-metal-catalyzed directing group-assisted inert Csp<sup>2</sup>-H functionalization has pooled up powerful strategies into modern chemistry toolbox in the last decade. The regioselective activation and annulation of C<img>H bonds are improving the synthetic approach and revolutionizing conventional cross-coupling techniques in current research. In this domain, the selective functionalization of C<img>H bonds in heteroarenes is primarily accomplished by Ru, Rh, Ir, and Pd metal complexes and their salts. This review primarily focuses on recent developments in the selective activation and functionalization of C<img>H bonds and the annulation of phthalazinones to synthesize their fused polycyclic frameworks. It explores their interactions with metal catalysts, along with various coupling partners such as amides, imides, ynones, vinylene carbonates, propargyl alcohols, alkenes, and alkynes which in turn led to the formation of different types of C<img>C and C<img>N bonds through selective C<img>H bond activation and subsequent annulation leading to pi-extended heterocycles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155618"},"PeriodicalIF":1.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917579","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 synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via oxidative cyclization of benzothiohydrazides and aldehydes catalyzed by tetra-n-butylammonium iodide 四正丁基碘化铵催化苯并噻唑和醛的氧化环化电化学合成2,5-二取代-1,3,4-噻二唑
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-21 DOI: 10.1016/j.tetlet.2025.155606
Kemparajegowda , Rajaghatta N. Suresh , Toreshettahally R. Swaroop , Muddegowda Umashankara , Kempegowda Mantelingu , Kanchugarakoppal S. Rangappa
{"title":"Electrochemical synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via oxidative cyclization of benzothiohydrazides and aldehydes catalyzed by tetra-n-butylammonium iodide","authors":"Kemparajegowda ,&nbsp;Rajaghatta N. Suresh ,&nbsp;Toreshettahally R. Swaroop ,&nbsp;Muddegowda Umashankara ,&nbsp;Kempegowda Mantelingu ,&nbsp;Kanchugarakoppal S. Rangappa","doi":"10.1016/j.tetlet.2025.155606","DOIUrl":"10.1016/j.tetlet.2025.155606","url":null,"abstract":"<div><div>In this letter, we present the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles by the oxidative cyclization reaction between benzothiohydrazides and aldehydes. The reaction mixture is electrolyzed by using reticulated vitreous carbon (RVC) and platinum as anode and cathode respectively. The tetra-<em>n</em>-butylammonium iodide played dual role as supporting electrolyte as well as catalyst. Further, this method is an example for green organic synthesis since it avoids the need of stoichiometric amount of oxidants and atom economies are high.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155606"},"PeriodicalIF":1.5,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143852215","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
Stereoselective access to bioactive cyclopropanes (+)-PPCC and (1R,2S)-2-aminomethyl-1-arylcyclopropane-1-carboxamides from (−)-levoglucosenone 立体选择性地从（−）左旋葡萄糖酮中获得生物活性环丙烷(+)-PPCC和(1R,2S)-2-氨基甲基-1-芳基环丙烷-1-羧酰胺
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-18 DOI: 10.1016/j.tetlet.2025.155620
Edward T. Ledingham, Johannes Puschnig, Ben W. Greatrex
{"title":"Stereoselective access to bioactive cyclopropanes (+)-PPCC and (1R,2S)-2-aminomethyl-1-arylcyclopropane-1-carboxamides from (−)-levoglucosenone","authors":"Edward T. Ledingham,&nbsp;Johannes Puschnig,&nbsp;Ben W. Greatrex","doi":"10.1016/j.tetlet.2025.155620","DOIUrl":"10.1016/j.tetlet.2025.155620","url":null,"abstract":"<div><div>The chiral synthon (−)-levoglucosenone (LGO) obtained from cellulose pyrolysis has been transformed into two known bioactive compounds: the serotonin-norepinephrine-dopamine reuptake inhibitor (1<em>R</em>,2<em>S</em>)-2-(aminomethyl)-<em>N</em>,<em>N</em>-diethyl-1-(naphthalen-2-yl)cyclopropane-1-carboxamide and the σ<sub>−</sub>receptor ligand (+)-PPCC. The key steps in the process were the arylation of an LGO derivative via a Suzuki-Miyaura cross-coupling reaction, then cyclopropanation under Johnson-Corey-Chaykovsky conditions. Dehomologation was achieved using Baeyer-Villiger and NaIO<sub>4</sub> mediated oxidation, and then functional group interconversion gave the bioactive cyclopropanes. Several derivatives of each target were developed demonstrating the versatility of the process for aryl and amine group substitution.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155620"},"PeriodicalIF":1.5,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143873717","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
Tamaru reaction-based approach towards the synthesis of muscone and analogues using renewable sources 基于Tamaru反应的可再生资源合成麝香酮及其类似物的方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-18 DOI: 10.1016/j.tetlet.2025.155593
Santosh J. Gharpure, Saidurga Prasad Kommyreddy
{"title":"Tamaru reaction-based approach towards the synthesis of muscone and analogues using renewable sources","authors":"Santosh J. Gharpure,&nbsp;Saidurga Prasad Kommyreddy","doi":"10.1016/j.tetlet.2025.155593","DOIUrl":"10.1016/j.tetlet.2025.155593","url":null,"abstract":"<div><div>Muscone is considered as the king of fragrances, due to its rare occurrence and exotic nature, many attempts have been made to synthesise musk analogues. The presence of methyl group at the C-3 position from ketone imparts the musk character to the molecule. The Tamaru reaction (Ni-catalysed reductive coupling of aldehyde and 1,3-dienes) is used as the key step for the installation of the methyl group in an efficient manner to afford the RCM precursor diene. A short three step sequence involving oxidation, RCM and reduction gave a highly efficient access to muscone and analogues. Both the precursors, namely, the aldehyde and isoprene are derived from renewable resource.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155593"},"PeriodicalIF":1.5,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143844459","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 chiral Azetidine and its application in asymmetric synthesis 手性氮杂啶的合成及其在不对称合成中的应用
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-17 DOI: 10.1016/j.tetlet.2025.155617
Xiyan Ren , Mengyao Xue , Xintong Yang , Yuting Yan , Kun Zhang , Jianhui Huang
{"title":"Synthesis of chiral Azetidine and its application in asymmetric synthesis","authors":"Xiyan Ren ,&nbsp;Mengyao Xue ,&nbsp;Xintong Yang ,&nbsp;Yuting Yan ,&nbsp;Kun Zhang ,&nbsp;Jianhui Huang","doi":"10.1016/j.tetlet.2025.155617","DOIUrl":"10.1016/j.tetlet.2025.155617","url":null,"abstract":"<div><div>Azetidine is a four-membered nitrogen-containing heterocycle, which has been utilized broadly in synthetic and medicinal chemistry. The use of azetidines in asymmetric catalysis remains largely unexplored, making this approach both innovative and promising for advancing the field. In this study, we designed and synthesized chiral bidentate azetidine pyridine hybrid ligands. A Pd-catalyzed asymmetric arylation of sulfonylimine with phenylboronic acid was examined using these new ligands. The chiral sulfonamides were obtained in excellent yields with low to good enantioselectivity (60:40 to 95:5 er).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155617"},"PeriodicalIF":1.5,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143860185","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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