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NH4I/TBHP-mediated synthesis of 2-aroylbenzothiazoles through [4 + 1] oxidative annulation of 2-aminothiophenols and aryl methyl ketones NH4I/ thbhp介导2-氨基噻吩和芳基甲基酮[4 + 1]氧化环合成2-芳基苯并噻唑
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-24 DOI: 10.1016/j.tetlet.2025.155750
Sasi Sree Marupalli, Venkatachalam Rajeshkumar
{"title":"NH4I/TBHP-mediated synthesis of 2-aroylbenzothiazoles through [4 + 1] oxidative annulation of 2-aminothiophenols and aryl methyl ketones","authors":"Sasi Sree Marupalli,&nbsp;Venkatachalam Rajeshkumar","doi":"10.1016/j.tetlet.2025.155750","DOIUrl":"10.1016/j.tetlet.2025.155750","url":null,"abstract":"<div><div>An efficient one-pot protocol has been established for the synthesis of 2-aroylbenzothiazoles by using the combination of NH<sub>4</sub>I/TBHP system. The reaction proceeds through NH<sub>4</sub>I/TBHP-mediated oxidation of aryl methyl ketones followed by annulation with sequential C<img>N and C<img>S bond formation. The process demonstrates smooth reactivity across a diverse range of aryl methyl ketones, producing the desired products in good to excellent yields. This method can also be easily scaled up to gram level, resulting in yield of up to 68 %.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155750"},"PeriodicalIF":1.5,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144695063","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
Advances in vicinal dicarbo-C–H-functionalization of five-membered heteroarenes via palladium/norbornene cooperative catalysis 钯/降冰片烯协同催化五元杂芳烃邻二碳-碳氢功能化研究进展
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-23 DOI: 10.1016/j.tetlet.2025.155742
Yun Zhou, Renhe Li, Rong Ye, Qi Zhu, Xin Liu, Guangbin Dong
{"title":"Advances in vicinal dicarbo-C–H-functionalization of five-membered heteroarenes via palladium/norbornene cooperative catalysis","authors":"Yun Zhou,&nbsp;Renhe Li,&nbsp;Rong Ye,&nbsp;Qi Zhu,&nbsp;Xin Liu,&nbsp;Guangbin Dong","doi":"10.1016/j.tetlet.2025.155742","DOIUrl":"10.1016/j.tetlet.2025.155742","url":null,"abstract":"<div><div>Direct introduction of two carbon substituents to less functionalized aromatic cores has been an attractive objective for late-stage modification and streamlined synthesis of complex molecules. Using the palladium/norbornene (Pd/NBE) cooperative catalysis, while initial achievements on double C<img>H functionalization were made in the past, the scopes of reactions and substrates remain to be expanded. Here we report some new advances on the Pd/NBE-catalyzed dicarbofunctionalization of five-membered heteroarenes through sequential C<img>H activation. These efforts include the Pd/NBE-catalyzed C4-arylation/C5-alkenylation of diverse furans, the first C4-alkynylation of thiophenes/pyrroles, and the preliminary C4-methylation.</div><div>2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155742"},"PeriodicalIF":1.5,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144685437","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
Sodium stearate-mediated heck and heck cassar sonogashira reactions: aqueous micellar catalysis at room temperature 硬脂酸钠介导的heck和heck cassar sonogashira反应：室温下的水性胶束催化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-23 DOI: 10.1016/j.tetlet.2025.155744
Kinjal Markana , Archana Cholera , Sunil Gadakh , Tushar Patel , Neha Baku , K.D. Ladva
{"title":"Sodium stearate-mediated heck and heck cassar sonogashira reactions: aqueous micellar catalysis at room temperature","authors":"Kinjal Markana ,&nbsp;Archana Cholera ,&nbsp;Sunil Gadakh ,&nbsp;Tushar Patel ,&nbsp;Neha Baku ,&nbsp;K.D. Ladva","doi":"10.1016/j.tetlet.2025.155744","DOIUrl":"10.1016/j.tetlet.2025.155744","url":null,"abstract":"<div><div>This study presents a novel and efficient protocol for Heck and Heck Cassar Sonogashira cross-coupling reactions, employing sodium stearate surfactant (SSS) as a micellar catalyst in aqueous media. Sodium stearate, a readily available and cost-effective soap-based surfactant, demonstrates superior catalytic performance compared to conventional surfactants such as TPGS-750M and traditional heating methods. The proposed methodology offers several distinct advantages, including reduced manufacturing costs, improved isolated yields, enhanced scalability, minimized waste generation, and increased chemical recyclability. These factors collectively make this approach both economically and environmentally sustainable. Sodium stearate efficiently facilitates high reaction conversions, leading to excellent yields of the desired coupling products under mild aqueous conditions. This protocol proves particularly valuable for the syn thesis of essential drug molecules, including Kedarcidin chromophore, 5-fluorouracil, Dynemicin-A, Pyr rhoxanthin, and Phorbazole-A. The development of this alternative address’s critical challenges in pharmaceutical research and industrial applications by enabling the efficient production of key pharmacophores.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155744"},"PeriodicalIF":1.5,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144685436","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
Iridium-catalyzed regioselective hydroalkylation of terminal Allenes with malonic amides 铱催化末端烯烯与丙二烯酰胺的区域选择性烷基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-22 DOI: 10.1016/j.tetlet.2025.155759
Takahiro Sawano , Ami Iwasa , Ayumu Sugiyama , Kengo Honda , Ryo Takeuchi
{"title":"Iridium-catalyzed regioselective hydroalkylation of terminal Allenes with malonic amides","authors":"Takahiro Sawano ,&nbsp;Ami Iwasa ,&nbsp;Ayumu Sugiyama ,&nbsp;Kengo Honda ,&nbsp;Ryo Takeuchi","doi":"10.1016/j.tetlet.2025.155759","DOIUrl":"10.1016/j.tetlet.2025.155759","url":null,"abstract":"<div><div>We report the regioselective hydroalkylation of terminal allenes with malonic amides by a cooperative catalyst consisting of a cationic iridium catalyst and an acid catalyst. The hydroalkylation proceeded in a highly atom-economical manner. The hydroalkylated product can be converted to a γ,δ-unsaturated amide through deaminocarbonylation. Several experiments on the reaction mechanism indicated that the linear allylic ester formed by the addition of trifluoroacetic acid to allene is a possible intermediate in the reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155759"},"PeriodicalIF":1.5,"publicationDate":"2025-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144714454","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
Recent advances of synthetic strategies toward macrocyclic drugs 大环类药物合成策略研究进展
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-22 DOI: 10.1016/j.tetlet.2025.155760
Fei Liu, Xiaolong Min
{"title":"Recent advances of synthetic strategies toward macrocyclic drugs","authors":"Fei Liu,&nbsp;Xiaolong Min","doi":"10.1016/j.tetlet.2025.155760","DOIUrl":"10.1016/j.tetlet.2025.155760","url":null,"abstract":"<div><div>Macrocyclic drugs, which are characterized by ring structures composed of more than 12 atoms, often exhibit enhanced druggability due to the incorporation of macrocyclic scaffolds. In recent years, these compounds have garnered increasing attention from pharmacologists, with a growing number of macrocyclic drugs receiving regulatory approval. Constructing the macrocyclic framework is inherently challenging, and the selection of an appropriate strategy for macrocycle synthesis is essential for improving the efficiency of drug development. This review examines the macrocyclic construction strategies employed in FDA-approved drugs and those in clinical development over the past decade, with the aim of attracting further interest from chemists and advancing progress in this area.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155760"},"PeriodicalIF":1.5,"publicationDate":"2025-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144702442","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 functionalized cyclopropanes from alkyl pinacol boronates by a radical polar cyclization cascade 用自由基极性环化级联法制备硼酸烷基松醇功能化环丙烷
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-22 DOI: 10.1016/j.tetlet.2025.155757
Zhen-Ye Wu , Qing Liu , Tian-Le Huang , Li Hai , Yong Wu
{"title":"Synthesis of functionalized cyclopropanes from alkyl pinacol boronates by a radical polar cyclization cascade","authors":"Zhen-Ye Wu ,&nbsp;Qing Liu ,&nbsp;Tian-Le Huang ,&nbsp;Li Hai ,&nbsp;Yong Wu","doi":"10.1016/j.tetlet.2025.155757","DOIUrl":"10.1016/j.tetlet.2025.155757","url":null,"abstract":"<div><div>Herein, we report a novel strategy for the synthesis of functionalized cyclopropanes via a photoredox-catalyzed radical addition-polar cyclization cascade. This reaction enables efficient cyclopropane assembly via a radical-polar crossover-mediated reductive termination between alkyl pinacol boronates and electron-deficient alkenes, generating carbanion intermediates that undergo intramolecular alkylation to complete the strained ring formation. This work, achieving the synthesis of 28 cyclopropane derivatives with up to 85 % yield, not only provides a versatile toolbox for strained ring synthesis but also advances the fundamental understanding of boron radical chemistry in photoredox systems.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155757"},"PeriodicalIF":1.5,"publicationDate":"2025-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144714385","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 route to dihydrofuran fused naphthoquinones via gold-catalyzed oxyarylation of alkenes 金催化烯烃氧芳化制二氢呋喃融合萘醌的途径
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-19 DOI: 10.1016/j.tetlet.2025.155755
Chandrakant B. Nichinde , Emilay B.T. Diogo , Renata G. Almeida , Eufrânio N. da Silva Júnior , Nitin T. Patil
{"title":"A route to dihydrofuran fused naphthoquinones via gold-catalyzed oxyarylation of alkenes","authors":"Chandrakant B. Nichinde ,&nbsp;Emilay B.T. Diogo ,&nbsp;Renata G. Almeida ,&nbsp;Eufrânio N. da Silva Júnior ,&nbsp;Nitin T. Patil","doi":"10.1016/j.tetlet.2025.155755","DOIUrl":"10.1016/j.tetlet.2025.155755","url":null,"abstract":"<div><div>A ligand-assisted Au(I)/Au(III) catalytic approach has been developed to achieve 1,2-oxyarylation of alkenes for the efficient synthesis of dihydrofuran-fused naphthoquinones. This redox-neutral method leverages the π-acidic properties of MeDalPhosAuCl to facilitate 1,2-difunctionalization under mild conditions, eliminating the need for external oxidants or photocatalysts. The strategy exhibits broad substrate scope, employing readily available, non-prefunctionalized aryl iodides, and provides a valuable route to structurally complex heterocycles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155755"},"PeriodicalIF":1.5,"publicationDate":"2025-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144704327","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
Assembly of thiazole-2-thiones through cyclization of enaminones, aryl isothiocyanates, and elemental sulfur 通过胺酮、芳基异硫氰酸酯和单质硫的环化组装噻唑-2-硫酮
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-18 DOI: 10.1016/j.tetlet.2025.155748
Tan N. Huynh , Phong D. Nguyen , Vu H. Luu , Truong K. Chau , Anh T. Nguyen , Tung T. Nguyen , Nhan T.H. Le
{"title":"Assembly of thiazole-2-thiones through cyclization of enaminones, aryl isothiocyanates, and elemental sulfur","authors":"Tan N. Huynh ,&nbsp;Phong D. Nguyen ,&nbsp;Vu H. Luu ,&nbsp;Truong K. Chau ,&nbsp;Anh T. Nguyen ,&nbsp;Tung T. Nguyen ,&nbsp;Nhan T.H. Le","doi":"10.1016/j.tetlet.2025.155748","DOIUrl":"10.1016/j.tetlet.2025.155748","url":null,"abstract":"<div><div>Synthesis of thiazole-2-thiones is often challenging as it requires the use of flammable, toxic CS<sub>2</sub> as the sulfur source. Only a couple of examples in which elemental sulfur provides sulfur atoms for thiazole-2-thiones are known. Yet, those methods often suffer from over-stoichiometric amount of a strong oxidant and the limitation of substrate scope. Herein we develop a method to allow for a three-component annulation of enaminones, aryl isothiocyanates, and elemental sulfur to target 5-benzoylthiazole-2-thiones. Our successes feature a new approach in which relatively electron-rich C<img>C bonds in enaminones are utilized to afford thiazole-2-thiones without the assistance of external oxidants.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155748"},"PeriodicalIF":1.5,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144657107","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 dehydrogenation of Indolines 可见光诱导吲哚的脱氢反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-18 DOI: 10.1016/j.tetlet.2025.155753
Jin Feng, Hao Guo, Aishun Ding
{"title":"Visible-light-induced dehydrogenation of Indolines","authors":"Jin Feng,&nbsp;Hao Guo,&nbsp;Aishun Ding","doi":"10.1016/j.tetlet.2025.155753","DOIUrl":"10.1016/j.tetlet.2025.155753","url":null,"abstract":"<div><div>The indole structure, commonly found in natural products and pharmaceuticals, draws attention for its potential in liquid organic hydrogen carriers, leading to interest in the transformation between indolines and indoles. Here, a protocol utilizing visible light for the dehydrogenation of indolines is developed, employing thioxanthone (TX) as photocatalyst and di-<em>tert</em>-butyl peroxide (DTBP) as oxidant. In this method, DTBP is excited through the energy transfer (EnT) process with TX*, resulting in the homolysis and the formation of crucial <em>tert</em>-butoxy radicals. These radicals then facilitate a two-step hydrogen atom transfer (HAT) process with the substrate to yield indoles. The entire dehydrogenation has latent practicability due to its broad substrate compatibility and mild reaction conditions, which further expands the application of TX in the organophotocatalytic field.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155753"},"PeriodicalIF":1.5,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144695064","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
Thiobenzoic acid–catalyzed radical–radical cross–coupling between benzyl alcohols and benzophenones via hydrogen atom transfer 巯基苯甲酸通过氢原子转移催化苯甲醇和二苯甲酮之间的自由基-自由基交叉偶联
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-17 DOI: 10.1016/j.tetlet.2025.155752
Riku Osanai, Kaichi Watanabe, Hiromichi Egami, Yoshitaka Hamashima
{"title":"Thiobenzoic acid–catalyzed radical–radical cross–coupling between benzyl alcohols and benzophenones via hydrogen atom transfer","authors":"Riku Osanai,&nbsp;Kaichi Watanabe,&nbsp;Hiromichi Egami,&nbsp;Yoshitaka Hamashima","doi":"10.1016/j.tetlet.2025.155752","DOIUrl":"10.1016/j.tetlet.2025.155752","url":null,"abstract":"<div><div>The radical-radical cross-coupling of benzyl alcohols with benzophenones was successfully demonstrated by using thiobenzoic acid as a multifunctional photocatalyst. The reaction proceeded smoothly under visible-light irradiation to afford the corresponding diols in good yield and various functional groups were well tolerated. Furthermore, the catalytic system was also applicable to prenyl alcohol and benzylamine. Mechanistically, the excited state of thiobenzoate acts as a single electron reducing agent for benzophenones and the resulting sulfur radical promotes hydrogen atom abstraction from benzyl alcohols.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155752"},"PeriodicalIF":1.5,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144685438","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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