Cheng Cheng, Yiru Pan, Yuhong Gao, Jisheng Luo, Li Deng
{"title":"Organocatalytic asymmetric umpolung reaction of cyanoketimines with 2-(bromomethyl)acrylate","authors":"Cheng Cheng, Yiru Pan, Yuhong Gao, Jisheng Luo, Li Deng","doi":"10.1016/j.tetlet.2025.155722","DOIUrl":"10.1016/j.tetlet.2025.155722","url":null,"abstract":"<div><div>Chiral α-aminonitriles are not only versatile synthons in chemical synthesis, but also exist as motifs in a wide range of biologically active molecules. Consequently, the catalytic asymmetric synthesis of chiral α-aminonitriles has attracted considerable attention. Despite these significant progresses, the catalytic asymmetric synthesis of chiral α-aminonitriles bearing other synthetically useful functionalities remains desirable. We reported a catalytic asymmetric synthesis of chiral α-aminonitriles bearing a 2‑carbonyl allyl group <em>via</em> a catalytic umpolung reaction of cyanoketimines with 2-(bromomethyl)acrylate. This reaction demonstrates broad substrate scope, accommodating a wide range of aryl, heteroaryl and alkyl cyanoketimines. Given that both the aminonitrile and the 2‑carbonyl allyl moieties are versatile synthons in asymmetric synthesis, we anticipate that this reaction will serve as a valuable method for drug discovery and construction of complex chiral molecules.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155722"},"PeriodicalIF":1.5,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144518185","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}
Cheng-Cheng Wei, Yu-Mei Zhang, Yi Li, Mei-Hua Shen, Hua-Dong Xu
{"title":"Copper catalyzed cyclization of N-propargyl-N-tosyl hydrazines: Facile preparation of 1,5-disubstituted pyrazoles","authors":"Cheng-Cheng Wei, Yu-Mei Zhang, Yi Li, Mei-Hua Shen, Hua-Dong Xu","doi":"10.1016/j.tetlet.2025.155721","DOIUrl":"10.1016/j.tetlet.2025.155721","url":null,"abstract":"<div><div>A CuBr∙SMe<sub>2</sub> catalyzed intramolecular cyclization of N-tosy-N-propargyl hydrazine derivatives to form N-substituted pyrazoles was established, presumably, through a one-pot-two-step domino of 5-<em>endo</em>-dig cyclization and subsequent eliminative aromatization. Nineteen N-substituted pyrazoles were made with good to excellent yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155721"},"PeriodicalIF":1.5,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144501090","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}
Debopam Pal , Dhruvilkumar Sureshkumar Patel , Vishnumaya Bisai
{"title":"Catalytic asymmetric synthesis and Stereocenter assignment of naturally occurring Sesquiterpenoid, (−)-Baccharisketone","authors":"Debopam Pal , Dhruvilkumar Sureshkumar Patel , Vishnumaya Bisai","doi":"10.1016/j.tetlet.2025.155719","DOIUrl":"10.1016/j.tetlet.2025.155719","url":null,"abstract":"<div><div>Catalytic asymmetric total synthesis of either enantiomer of naturally occurring sesquiterpenoid, i.e. (−)-baccharisketone (<strong>1a</strong>) and (+)-baccharisketone (<em>ent</em>-<strong>1a</strong>) has been achieved via a key catalytic asymmetric <em>p</em>-tolyl boronic acid addition onto <em>E</em>-ester. Thus, an efficient five-step approach to both enantiomers of baccharisketone has been shown using 2 mol% Rh(COD)<sub>2</sub>BF<sub>4</sub>-(<em>R</em>)-BINAP as catalyst to achieve the product with a stereogenic center at the pseudobenzylic position (up to 93 % ee). This also confirms the assignment of the stereogenic center present at the pseudobenzylic position.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155719"},"PeriodicalIF":1.5,"publicationDate":"2025-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144492066","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}
Mansi Dubey, Satyanand Kumar, Ravi Kumar, Satish Kumar Awasthi
{"title":"Gold nanoparticles for selective aromatic fluorine substitution by Azide under moderate conditions: Insights and mechanistic studies via DFT","authors":"Mansi Dubey, Satyanand Kumar, Ravi Kumar, Satish Kumar Awasthi","doi":"10.1016/j.tetlet.2025.155712","DOIUrl":"10.1016/j.tetlet.2025.155712","url":null,"abstract":"<div><div>A newer method was serendipitously discovered and exploited for the synthesis of various aromatic azides. By reacting fluoro-substituted aryl derivatives with sodium azide under conventional heating in DMF and using gold nanoparticles as suitable catalysts, selective aromatic fluorine substitution via the S<sub>N</sub>Ar mechanism was achieved. This approach led to the formation of some novel aromatic azides with high yields and shorter reaction times.<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (405KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155712"},"PeriodicalIF":1.5,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144556705","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}
{"title":"ZnBr2 catalyzed sequential A3-coupling and intramolecular cyclization: One-pot synthesis of 3-aminofurans","authors":"Battini Geetha Rani , Sreedhar Gundekari , Kola Ramesh , Chandra Sekhar Vasam , Narasimha Swamy Thirukovela","doi":"10.1016/j.tetlet.2025.155718","DOIUrl":"10.1016/j.tetlet.2025.155718","url":null,"abstract":"<div><div>ZnBr<sub>2</sub> salt was observed to be an effective catalyst to promote domino A<sup>3</sup>-coupling and intramolecular cyclization for the synthesis of 3-aminofurans from simple and commercially available α-ketoaldehydes, secondary amines, and terminal alkynes as starting materials. This method is compatible with several substrates and attractive, due to the formation of water as a by-product, operational simplicity, atom-economy, shorter reaction time, and inexpensive catalyst.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155718"},"PeriodicalIF":1.5,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144501394","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}
Run He, Zilong Zhang, Yuxiang Zhou, Li Zeng, Lou Shi, Deqiang Liang
{"title":"t-BuOLi-promoted Knoevenagel condensation: An efficient approach for synthesizing Arylid-BOX","authors":"Run He, Zilong Zhang, Yuxiang Zhou, Li Zeng, Lou Shi, Deqiang Liang","doi":"10.1016/j.tetlet.2025.155706","DOIUrl":"10.1016/j.tetlet.2025.155706","url":null,"abstract":"<div><div>A <em>t</em>-BuOLi-promoted Knoevenagel condensation is reported, offering a straightforward method for the rapid construction of Arylid-BOX. This late-stage functionalization method of unsubstituted BOX ligands enables the rapid synthesis of a wide range of Arylid-BOX compounds. We speculate that the relatively small atomic radius of lithium ions contributes to the high yields of this reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155706"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144307133","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}
{"title":"Mercaptan-free approach to the synthesis of Ethiprole, an insecticide","authors":"Rachel Gundamalla , P. Naveen Reddy , RajashakerBantu , B.V. Subba Reddy","doi":"10.1016/j.tetlet.2025.155713","DOIUrl":"10.1016/j.tetlet.2025.155713","url":null,"abstract":"<div><div>An efficient and practical method has been developed for the synthesis of a second-generation insecticide, ethiprole. The key step involved in this approach is the thiocynation of pyrazole ring at the 4th position, which was achieved using bromine and potassium thiocyanate in methanol. Another important step involves the one-pot conversion of thiocyanate into ethyl sulfide using ethyl bromide in the presence of a base. Each step in this synthesis was performed efficiently on a gram scale to produce high-quality product. This new synthetic strategy is simple, convenient and scalable.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155713"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329791","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}
Badrinath N. Kakde , Suman Noskar , Saikat Bag , Alakesh Bisai
{"title":"Total syntheses of anticancer Abietane Diterpenoids, (±)-Royleanone and (±)-Inuroyleanol via Lewis acid catalyzed Hydroarylation","authors":"Badrinath N. Kakde , Suman Noskar , Saikat Bag , Alakesh Bisai","doi":"10.1016/j.tetlet.2025.155715","DOIUrl":"10.1016/j.tetlet.2025.155715","url":null,"abstract":"<div><div>Herein we report a Lewis acid-catalyzed intramolecular hydroarylation strategy enabling an efficient synthesis of [6,6,6]-fused abietane diterpenoids sharing a trans-decalin motif. Using bismuth(III) triflate as an efficient metal triflate, the key intermediates were prepared in high yields, facilitating concise total syntheses of royleanone (<strong>1a</strong>) and inuroyleanone (<strong>1c</strong>), showcasing a scalable approach to complex natural product frameworks.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155715"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329790","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}
Hai-Bing Long, Xue-Hua Huang, Da-Xian You, Ye Liang, Jin-Bao Peng, Jia-Lei Yan, Ai-Jun Ma
{"title":"An efficient synthesis of Indolo[3,2-c]coumarins by Pd-catalyzed intramolecular CH carbonylation","authors":"Hai-Bing Long, Xue-Hua Huang, Da-Xian You, Ye Liang, Jin-Bao Peng, Jia-Lei Yan, Ai-Jun Ma","doi":"10.1016/j.tetlet.2025.155716","DOIUrl":"10.1016/j.tetlet.2025.155716","url":null,"abstract":"<div><div>Indolo[3,2-<em>c</em>]coumarins, characterized by their distinctive fused heterocyclic architecture, demonstrate significant biological activities in natural settings. In this study, we report a Pd-catalyzed intramolecular C<img>H carbonylation methodology for the synthesis of indolo[3,2-<em>c</em>]coumarins, and provide a straightforward approach for the total synthesis of natural product derivative and bioactive molecule of this class. This novel methodology provides a versatile platform for the comprehensive synthesis of indolo[3,2-<em>c</em>]coumarins.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155716"},"PeriodicalIF":1.5,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144338692","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}
Pei Liu , Wei Du , Yu-An Feng , Yu-Bin Su , Ya-Wen Wang , Jian Xiao , Yu Peng
{"title":"Highly sensitive turn-on fluorescent probe for the specific detection of cadaverine in shrimp","authors":"Pei Liu , Wei Du , Yu-An Feng , Yu-Bin Su , Ya-Wen Wang , Jian Xiao , Yu Peng","doi":"10.1016/j.tetlet.2025.155714","DOIUrl":"10.1016/j.tetlet.2025.155714","url":null,"abstract":"<div><div>An organic small-molecule fluorescent probe <strong>SWJT-36</strong> with an isophorone backbone for the specific detection of cadaverine (Cad), a shrimp spoilage marker, was developed. After the reaction the solution exhibited a distinct color change from pale yellow to deep amber under visible light irradiation, accompanied by intense red fluorescence emission. Particularly, <strong>SWJT-36</strong> exhibited high selectivity, low detection limit (2.655 μM), and fast response (t<sub>1/2</sub> = 13.8 min) for Cad. The reaction mechanism of <strong>SWJT-36</strong> and Cad was determined by mass spectrometry. And <strong>SWJT-36</strong> could be made into portable test strips that could detect Cad, thereby detecting the freshness of shrimp.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155714"},"PeriodicalIF":1.5,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144307134","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}